DE2840010C3 - Graft copolymers - Google Patents
Graft copolymersInfo
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- DE2840010C3 DE2840010C3 DE2840010A DE2840010A DE2840010C3 DE 2840010 C3 DE2840010 C3 DE 2840010C3 DE 2840010 A DE2840010 A DE 2840010A DE 2840010 A DE2840010 A DE 2840010A DE 2840010 C3 DE2840010 C3 DE 2840010C3
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F251/00—Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof
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Description
Die Erfindung betrifft Pfropfmischpolymerisate mit Struktureinheiten, die auf ein Polysaccharid und ein wasserlösliches Monomeres zurückgehen.The invention relates to graft copolymers with structural units which are based on a polysaccharide and a water-soluble monomer.
Durch Aufpfropfen wasserlöslicher Monomerer auf Kohlenhydrate erhaltene Polymerisate finden vielfältige Verwendung in der Technik, z. B. als Mittel zur Füllstoffretention bei der Papierherstellung, als Klebstoffe, Schlichtmittel, Flockungsmittel, Ionenaustauschharze, Bohrschlammzusätze und Wasseraufbereitungsmittel.Polymers obtained by grafting water-soluble monomers onto carbohydrates have a wide range of uses in technology, e.g. B. as agents for filler retention in papermaking, as adhesives, sizing agents, flocculants, ion exchange resins, drilling mud additives and water treatment agents.
Verfahren zur Herstellung von Pfropfmischpolymerisaten von Polysacchariden, wie Stärke, Cellulose und Gummi, sind nach der Literatur bekannt, z. B. aus "Block and Graft Copolymerization", Vol. 1, R. J. Ceresa, herausgegeben von John Wiley und Söhne (1973). Derartige Verfahren, die auch in den US-PS 38 09 664 und 39 76 552 beschrieben werden, umfassen Polymerisationen in Wasser, in Mischungen aus Wasser und einem Lösungsmittel und in trockenem Zustand. Diese können durch Bestrahlung sowie mechanisch und chemisch initiiert werden.Process for the preparation of graft copolymers of polysaccharides, such as starch, cellulose and gum, are known from the literature, e.g. B. from "Block and Graft Copolymerization", Vol. 1, R. J. Ceresa, edited by John Wiley and Sons (1973). Such processes, which are also described in US-PS 38 09 664 and 39 76 552, comprise polymerizations in water, in mixtures of water and a solvent and in the dry state. These can be initiated by irradiation as well as mechanically and chemically.
Die meisten der oben beschriebenen Verfahren sind jedoch für ein wirksames Aufpfropfen von wasserlöslichen Monomeren in wäßrigem Medium, in dem die Polymerisation mit diesen Monomeren äußerst vorteilhaft abläuft, insbesondere wenn chemische Initiatoren eingesetzt werden, relativ ungeeignet. Dieses nicht effektive Aufpfropfen geht hauptsächlich auf die starke Tendenz dieser Monomeren zur Ausbildung gesonderter nicht gepfropfter Polymerisate in der wäßrigen Phase zurück. Für ein wirksames Aufpfropfen ist es erforderlich, das Polysaccharidsubstrat und das wasserlösliche Monomer bzw. die Monomeren in sehr engen Kontakt zu halten, d. h. in hoher Konzentration im Hinblick auf das wäßrige Polymerisationsmedium. Auf diese Weise wird die Pfropfpolymerisation die vorherrschende Reaktion und die Tendenz zur Bildung von nicht gepfropften Polymerisaten auf ein Minimum zurückgeführt.Most of the processes described above, however, are relatively unsuitable for effective grafting of water-soluble monomers in an aqueous medium in which the polymerization with these monomers proceeds extremely advantageously, especially when chemical initiators are used. This ineffective grafting is mainly due to the strong tendency of these monomers to form separate ungrafted polymers in the aqueous phase. For effective grafting, it is necessary to keep the polysaccharide substrate and the water-soluble monomer or monomers in very close contact; H. in high concentration with respect to the aqueous polymerization medium. In this way, the graft polymerization, the predominant reaction and the tendency towards the formation of ungrafted polymers, are reduced to a minimum.
Mehrere Faktoren verhindern jedoch das Aufpfropfen von wasserlöslichen Monomeren auf Polysaccharidsubstrate in hoch konzentrierten wäßrigen Medien. Bei wasserlöslichen oder dispergierten Substraten, wie Cellulosederivaten, Gummiarten und Kochstärken, sind die Viskositäten einer wäßrigen Lösung mit selbst niedriger Konzentration (10 bis 20%) an Polysaccharid in Wasser untragbar hoch und nicht zu bewältigen. So ist es nicht möglich, ein wasserlösliches Monomer, z. B. Acrylsäure, auf ein in Wasser gelöstes oder dispergiertes Polysaccharidsubstrat bei z. B. 70% Feststoffgehalt aufzupfropfen. Beim Einsatz nicht dispergierter Polysaccharidsubstrate, wie Cellulose und nicht gekochte Stärke, die heterogen in Wasser bis zu einem Feststoffgehalt von 40 bis 60% suspendiert werden können, quillt das einmal gebildete Pfropfprodukt in Wasser und zeigt während der Polymerisation sehr hohe Viskosität. Dieser Effekt führt gewöhnlich zur Koagulation der Reaktionsmischung, was sie für kommerzielle Zwecke untauglich macht.However, several factors prevent water soluble monomers from grafting onto polysaccharide substrates in highly concentrated aqueous media. In the case of water-soluble or dispersed substrates, such as cellulose derivatives, gums and starches, the viscosities of an aqueous solution with even a low concentration (10 to 20%) of polysaccharide in water are prohibitively high and cannot be managed. So it is not possible to use a water-soluble monomer, e.g. B. acrylic acid, on a dissolved or dispersed in water polysaccharide substrate at z. B. grafting on 70% solids content. When using non-dispersed polysaccharide substrates, such as cellulose and uncooked starch, which can be heterogeneously suspended in water up to a solids content of 40 to 60%, the graft product once formed swells in water and shows a very high viscosity during polymerization. This effect usually leads to coagulation of the reaction mixture, making it unsuitable for commercial use.
Der Erfindung liegt die Aufgabe zugrunde, Pfropfmischpolymerisate der eingangs beschriebenen Art vorzuschlagen die einfacher und wirksamer in wäßrigen Medien bei hohen Konzentrationen erhalten werden können, wobei sie gleichzeitig in hoher Konzentration gebildet werden, ohne daß die auf die Viskosität zurückgehenden Probleme auftreten und sie insbesondere direkt aus der Reaktionsmischung in Form fester Kügelchen isoliert werden können.The invention is based on the object of proposing graft copolymers of the type described at the outset which can be obtained more easily and more effectively in aqueous media at high concentrations, while at the same time being formed in high concentrations without the problems related to viscosity occurring and, in particular, directly the reaction mixture can be isolated in the form of solid beads.
Erfindungsgemäß wird diese Aufgabe durch Pfropfmischpolymerisate gelöst, die dadurch erhalten sind, daßAccording to the invention this object is achieved by graft copolymers which are obtained in that
a) ein Polysaccharid in einem organischen Lösungsmittel, dessen Siedepunkt bei oder oberhalb der Reaktionstemperatur der Polymerisation liegt, das mit Wasser nicht mischbar ist und das Polysaccharid, das Monomer oder Pfropfmischpolymerisat nicht löst, suspendiert wird,a) a polysaccharide in an organic solvent whose boiling point is at or above the reaction temperature of the polymerization, which is immiscible with water and the polysaccharide, which does not dissolve the monomer or graft copolymer, is suspended,
b) dazu eine wäßrige Lösung des Monomers gegeben wird,b) an aqueous solution of the monomer is added,
c) die Reaktionsmischung von Sauerstoff befreit und in Gegenwart eines freie Radikale bildenden Polymerisationskatalysators auf 40 bis 100°C erhitzt wird,c) the reaction mixture is freed from oxygen and heated to 40 to 100 ° C in the presence of a polymerization catalyst which forms free radicals,
d) die Polymerisation 0,5 bis 6 Stunden fortgeführt wird undd) the polymerization continued for 0.5 to 6 hours will and
e) das gebildete Pfropfmischpolymerisat isoliert wird,e) the graft copolymer formed is isolated,
wobei die wäßrige Lösung und/oder die Suspension des Polysaccharids ein kationisches, anionisches oder nicht ionisches grenzflächenaktives Mittel enthält, der Feststoffgehalt der wäßrigen Polymerisationsmischung mehr als 50 Gew.-% beträgt und in dem fertigen Pfropfmischpolymerisat 10 bis 90 Gew.-% Polysaccharid vorliegen.the aqueous solution and / or the suspension of the polysaccharide containing a cationic, anionic or nonionic surface-active agent, the solids content of the aqueous polymerization mixture being more than 50% by weight and 10 to 90% by weight of polysaccharide being present in the finished graft copolymer.
Die erfindungsgemäßen Pfropfmischpolymerisate werden demzufolge aus Polysaccharidsubstraten und wasserlöslichen Monomeren unter eingeregelten Bedingungen hergestellt, so daß das Pfropfmischpolymerisat wirksam und bei hoher Umsetzung gebildet und ohne weiteres in Form fester Kügelchen isoliert werden kann.The graft copolymers according to the invention are accordingly prepared from polysaccharide substrates and water-soluble monomers under controlled conditions so that the graft copolymers can be formed effectively and with high conversion and can be readily isolated in the form of solid beads.
Wenn nachfolgend von dem "erfindungsgemäßen Verfahren" gesprochen wird, so soll darunter das Verfahren verstanden werden, nach dem die erfindungsgemäßen Pfropfmischpolymerisate herstellbar sind.When the “process according to the invention” is spoken of below, this is to be understood as the process by which the graft copolymers according to the invention can be produced.
Die Pfropfpolymerisation der erhaltenen Zweiphasenmischung wird in Gegenwart eines freie Radikale bildenden Katalysators unter Rühren und bei einer Temperatur von etwa 40 bis 100°C durchgeführt, wobei es erforderlich ist, daß mindestens eine der Phasen (d. h., das suspendierte Polysaccharid oder die wäßrige Lösung des Monomers) ein geeignetes grenzflächenaktives Mittel bzw. Netzmittel enthält. Es ist von Bedeutung, daß das organische Lösungsmittel, das in der Polysaccharidphase verwendet wird, mit der wäßrigen Lösungsphase des Monomers nicht mischbar ist, daß es nicht das Monomer oder das Pfropfmischpolymerisat, sobald es gebildet ist, löst und es einen Siedepunkt aufweist, der bei oder oberhalb der Polymerisationsreaktionstemperatur liegt.The graft polymerization of the two-phase mixture obtained is carried out in the presence of a catalyst which forms free radicals with stirring and at a temperature of about 40 to 100 ° C., it being necessary that at least one of the phases (ie the suspended polysaccharide or the aqueous solution of the monomer ) contains a suitable surfactant or wetting agent. It is important that the organic solvent used in the polysaccharide phase is immiscible with the aqueous solution phase of the monomer, that it does not dissolve the monomer or the graft copolymer once it is formed, and that it has a boiling point around or above the polymerization reaction temperature.
Nach dem erfindungsgemäßen Verfahren bildet die anfallende Mischung des suspendierten Polysaccharids und der wäßrigen Lösung des Monomers usw. eine diskontinuierliche Phase, die eine große Zahl diskreter Kugeln enthält, die in einer kontinuierlichen, nicht mischbaren organischen Lösungsmittelphase suspendiert sind, wobei jede Kugel in sich ein wäßriges Polymerisationssystem darstellt, das sowohl das PoIysaccharidsubstrat und das Monomer wie auch Wasser, den Katalysator und einen Puffer, sofern vorliegend, in solchen Anteilen enthält, daß der Feststoffgehalt mehr als 50 Gew.-% des gesamten wäßrigen Polymerisationssystems ausmacht. Diese Suspension diskreter Kugeln wird von Luft befreit und erhitzt, um die Polymerisation einzuleiten und ablaufen zu lassen. Die Kugeln behalten ihre Vollständigkeit während der Polymerisationsreaktion und werden mit Abschluß der Polymerisation ohne weiteres als Kügelchen oder in granulierter Form durch Filtration und Trocknen isoliert.According to the process of the invention, the resulting mixture of the suspended polysaccharide and the aqueous solution of the monomer etc. forms a discontinuous phase which contains a large number of discrete spheres suspended in a continuous, immiscible organic solvent phase, each sphere being an aqueous one Polymerization system which contains both the polysaccharide substrate and the monomer as well as water, the catalyst and a buffer, if present, in such proportions that the solids content makes up more than 50% by weight of the total aqueous polymerization system. This suspension of discrete spheres is de-aired and heated to initiate and allow the polymerization to proceed. The spheres retain their completeness during the polymerization reaction and are readily isolated as spheres or in granulated form by filtration and drying when the polymerization is complete.
Als Ergebnis der hohen Feststoffkonzentration, mit der die Polymerisationsreaktion durchgeführt wird, werden Pfropfmischpolymerisate hohen Pfropfausmaßes bzw. Pfropfgrades, im allgemeinen mehr als 75%, und hoher Umsetzung gebildet und können als solche nützlich einer Vielzahl von Verwendungszwecken zugeführt werden.As a result of the high solids concentration at which the polymerization reaction is carried out, graft copolymers of high degree of grafting, generally greater than 75%, and high conversion are formed and as such can be usefully put into a variety of uses.
Ein zusätzliches Merkmal des erfindungsgemäßen Verfahrens besteht darin, daß es die Herstellung von Pfropfmischpolymerisaten ermöglicht, die nachfolgend in Form von Zwischenprodukten ohne die Notwendigkeit der Isolierung mit anderen Reaktionsmitteln zur Umsetzung gebracht werden können.An additional feature of the process according to the invention is that it enables the preparation of graft copolymers which can subsequently be reacted with other reactants in the form of intermediates without the need for isolation.
Zu den bei der Durchführung des erfindungsgemäßen Verfahrens geeigneten Polysaccharidsubstraten zählen Stärken und Stärkeumsetzungsprodukte, die von beliebigen Pflanzen herstammen, Stärkeäther und -ester, Cellulose und Cellulosederivate und verschiedene Pflanzengummis. Die Substrate können in wasserlöslicher oder wasserunlöslicher Form verwendet werden.The polysaccharide substrates suitable for carrying out the method according to the invention include starches and starch conversion products which come from any plant, starch ethers and esters, cellulose and cellulose derivatives and various vegetable gums. The substrates can be used in water-soluble or water-insoluble form.
Stärken, die von Getreide, wie Mais und Weizen, Kartoffeln, Reis, Sago, Tapioka, Wachsmais, Sorghum und Amylose stammen sowie die Umsetzungsprodukte und Derivate davon, stellen die bevorzugten Substrate dar, was darauf zurückgeht, daß sie kostengünstig und leicht verfügbar sind.Starches derived from cereals such as corn and wheat, potatoes, rice, sago, tapioca, waxy corn, sorghum and amylose, and the reaction products and derivatives thereof, are the preferred substrates, due to their being inexpensive and readily available.
Die Menge des Polysaccharidsubstrats liegt zwischen 10 und 90 Gew.-%, vorzugsweise zwischen 40 und 70 Gew.-% des erfindungsgemäßen Pfropfmischpolymerisats.The amount of the polysaccharide substrate is between 10 and 90% by weight, preferably between 40 and 70% by weight of the graft copolymer according to the invention.
Das Polysaccharid wird in einem organischen Lösungsmittel suspendiert, wodurch eine kontinuierliche Phase gebildet wird, die gegebenenfalls ein lösungsmittellösliches grenzflächenaktives Mittel, das nachfolgend noch erläutert wird, in einer Menge von 1 bis 12 Gew.-% des Lösungsmittels enthalten kann. Bei dem ausgewählten Lösungsmittel muß es sich um ein mit Wasser nicht mischbares handeln, das das Polysaccharid oder das Monomer oder das Pfropfmischpolymerisat, so wie es gebildet wird, nicht löst und das einen Siedepunkt aufweist, der bei oder oberhalb der Temperatur liegt, bei der die Pfropfpolymerisationsreaktion durchgeführt wird. Geeignete Lösungsmittel können aromatische und aliphatische Kohlenwasserstoffe, wie auch gewisse chlorierte Kohlenwasserstoffe, darstellen, einschließlich Benzol, Dichlorbenzol, Toluol, Xylol, 1,2-Dichloräthan, Heptan, Octan, Isooctan und Nonan sowie andere Lösungsmittel, die der Fachmann aufgrund der angegebenen Parameter ohne weiteres auffinden kann. Mischungen solcher Lösungsmittel können ebenfalls eingesetzt werden.The polysaccharide is suspended in an organic solvent, thereby forming a continuous phase which may optionally contain a solvent-soluble surfactant, discussed below, in an amount of 1 to 12% by weight of the solvent. The solvent selected must be one which is immiscible with water, does not dissolve the polysaccharide or the monomer or the graft copolymer as it is formed, and which has a boiling point which is at or above the temperature at which the Graft polymerization reaction is carried out. Suitable solvents can be aromatic and aliphatic hydrocarbons, as well as certain chlorinated hydrocarbons, including benzene, dichlorobenzene, toluene, xylene, 1,2-dichloroethane, heptane, octane, isooctane and nonane as well as other solvents that the skilled person based on the parameters given without can find more. Mixtures of such solvents can also be used.
Die Monomeren, die in der Praxis für die Durchführung des erfindungsgemäßen Verfahrens geeignet sind, sind wasserlöslich (d. h., sie haben bei 25°C in Wasser eine minimale Löslichkeit von 5 Gew.-%), sind ungesättigt und zur Polymerisation durch Initiierung mittels freier Radikale fähig. Zu solchen Monomeren zählen Acrylsäure und Methacrylsäure, Acrylamid, Methacrylamid, Acrylonitril, N,N-Dialkylaminoalkylacrylate und -methacrylate (worin die Alkylgruppe 1 bis 4 Kohlenstoffatome enthält), äthylenisch ungesättigte quaternäre Ammoniumsalze, wie N,N,N-Trimethylaminoäthylmethacrylatmethylsulfat oder -halogenid, 2-Hydroxy-3-methacryloxypropyltrimethylammoniummethylsulfat oder -halogenid, Vinylbenzyltrialkylammoniummethylsulfat oder -halogenid, Dialkyldiallylammoniummethylsulfat oder -halogenid, Natrium- oder Ammoniumstyrolsulfonat, Vinylpyrrolidon, Hydroxyalkylacrylate und -methacrylate, Natrium-2-acrylamid-2-methylpropansulfonat usw. Verschiedene andere wasserlösliche Monomere, die zur Pfropfpolymerisation mit Polysacchariden geeignet sind, sind dem Fachmann gut bekannt.The monomers which are suitable in practice for carrying out the process according to the invention are water-soluble (ie they have a minimum solubility of 5% by weight in water at 25 ° C.), are unsaturated and are suitable for polymerization by initiation by means of free radicals able to. Such monomers include acrylic acid and methacrylic acid, acrylamide, methacrylamide, acrylonitrile, N, N-dialkylaminoalkyl acrylates and methacrylates (in which the alkyl group contains 1 to 4 carbon atoms), ethylenically unsaturated quaternary ammonium salts, such as N, N, N-trimethylaminoethyl methacrylate methyl sulfate or halide 2-Hydroxy-3-methacryloxypropyltrimethylammonium methyl sulfate or halide, vinylbenzyl trialkylammonium methyl sulfate or halide, dialkyldiallylammonium methyl sulfate or halide, sodium or ammonium styrenesulfonate, vinylpyrrolidone, water, monohydroxyalkylenesulfonate, others, vinylpyrrolidone, water, monohydroxyalkylenesulfonate, vinylpyrrolidone, other monomethylpyrrolidone, water, 2-methacrylamidate, vinylpyrrolidone, water, 2-methacrylamidate, vinylpyrrolidone, other, monomethylpyrrolidone, water, 2-methyl-acrylamidate, vinylpyrrolidone-water, methyl-2-acrylate, etc. are suitable for graft polymerization with polysaccharides are well known to those skilled in the art.
Die wasserlöslichen Monomeren können als einziger Bestandteil beim Pfropfen oder zusammen mit anderen Monomeren eingesetzt werden. Das Verhältnis und die Art des zusätzlich verwendeten Monomers hängt von den besonderen Bestandteilen und den vorgesehenen Endverwendungszwecken ab. So liegt die gesamte Menge des wasserlöslichen Monomers zwischen 10 und 90 Gew.-%, vorzugsweise zwischen 30 und 60 Gew.-%, des fertigen erfindungsgemäßen Pfropfpolymerisats.The water-soluble monomers can be used as the sole component in grafting or together with other monomers. The ratio and type of additional monomer used will depend on the particular ingredients and intended end uses. The total amount of the water-soluble monomer is between 10 and 90% by weight, preferably between 30 and 60% by weight, of the finished graft polymer according to the invention.
Das besondere Monomer oder die besonderen Monomere werden in Form einer wäßrigen Lösung eingesetzt, die auch ein wasserlösliches grenzflächenaktives Mittel in einer Menge von 0,5 bis 12 Gew.-%, bezogen auf das Polysaccharidsubstrat, enthalten kann. Die bei der Durchführung des erfindungsgemäßen Verfahrens eingesetzten Katalysatorsysteme stellen im allgemeinen solche dar, die nach der Literatur zum Aufpfropfen von besonderen Monomeren auf Polysaccharidsubstrate bekannt sind. Der gewählte besondere Katalysator muß selbstverständlich einen solchen Typ darstellen, bei dem der Initiator in der wäßrigen Phase der Reaktionsmischung, in der das Substrat und das Monomer vorliegen, gebildet wird. Auf diese Weise findet das Aufpfropfen durch die Erzeugung radikalischer Stellen direkt auf den Polysaccharidsubstraten oder durch Kettenübertragung auf das Substrat statt. Bei der Erfindung geeignete Katalysatorsysteme sind z. B. Cerammoniumnitrat, Wasserstoffperoxid/Eisen(II)-SaIz, anorganische Alkalimetall- oder Ammoniumpersulfate, organische Hydroperoxide usw. Sie können allein oder in Form von Redoxpaaren verwendet werden, d. h. in Zumischung mit Verbindungen mit reduzierender Wirkung, z. B. Alkalimetabisulfit oder Natriumformaldehydsulfoxylat. Die bevorzugten Katalysatoren stellen Ammonium- und Kaliumpersulfatsalze dar. Die Konzentration des eingesetzten Katalysators kann in dem Bereich von 0,1 bis 2 Gew.-%, bezogen auf den Polysaccharidbestandteil des Pfropfproduktes, liegen. Der Katalysator kann direkt zu der wäßrigen Monomerlösung oder zu der gesamten Reaktionsmischung in Form einer gesonderten Katalysatorlösung gegeben werden. Alternativ werden, wenn der Katalysator ein Redoxpaar aus einem wasserlöslichen Bestandteil und einem lösungsmittellöslichen Bestandteil enthält, derartige Bestandteile zu den jeweiligen Reaktionsphasen gegeben. Das angestrebte Aufpfropfen kann auch durch Bestrahlung der Reaktionsmischung eingeleitet werden.The particular monomer or monomers are used in the form of an aqueous solution which can also contain a water-soluble surfactant in an amount of 0.5 to 12% by weight, based on the polysaccharide substrate. The catalyst systems used in carrying out the process according to the invention are generally those which are known from the literature for grafting particular monomers onto polysaccharide substrates. The particular catalyst chosen must, of course, be of a type in which the initiator is formed in the aqueous phase of the reaction mixture in which the substrate and monomer are present. In this way, grafting occurs through the creation of free radical sites directly on the polysaccharide substrates or through chain transfer onto the substrate. In the invention suitable catalyst systems are, for. B. cerium ammonium nitrate, hydrogen peroxide / iron (II) salt, inorganic alkali metal or ammonium persulfates, organic hydroperoxides, etc. They can be used alone or in the form of redox couples, i. H. in admixture with compounds with a reducing effect, e.g. B. alkali metabisulfite or sodium formaldehyde sulfoxylate. The preferred catalysts are ammonium and potassium persulfate salts. The concentration of the catalyst used can be in the range from 0.1 to 2% by weight, based on the polysaccharide component of the graft product. The catalyst can be added directly to the aqueous monomer solution or to the entire reaction mixture in the form of a separate catalyst solution. Alternatively, if the catalyst contains a redox couple of a water-soluble component and a solvent-soluble component, such components are added to the respective reaction phases. The desired grafting can also be initiated by irradiating the reaction mixture.
Es wurde bereits vorstehend darauf hingewiesen, daß das grenzflächenaktive Mittel oder die grenzflächenaktiven Mittel, die bei der Herstellung des erfindungsgemäßen Pfropfmischpolymerisats verwendet werden, einen integrierten Bestandteil der Erfindung darstellen. Es ist in der Polysaccharidchemie bekannt, daß grenzflächenaktive Mittel dazu neigen, mit den Polysacchariden (einige mehr als andere) zu reagieren, so daß die Dispergierbarkeit des Polysaccharids in Wasser durch die Gegenwart eines grenzflächenaktiven Mittels herabgesetzt wird (vgl. z. B. Gray, Virginia M., et al., Die Stärke, 14, S. 239-246 [1962]). Das Polysaccharid und das grenzflächenaktive Mittel bilden einen Komplex, der die Dispergierbarkeit des Polysaccharids in Wasser im Vergleich zu der Dispergierbarkeit ohne grenzflächenaktives Mittel herabsetzt. In Abwesenheit des grenzflächenaktiven Mittels koagulieren die Kügelchen des Pfropfproduktes während der Polymerisation, wobei die Suspensionscharakteristiken der Reaktionsmischung aufgehoben werden und das Polymerisat schwer handhabbar gemacht wird.It has already been pointed out above that the surface-active agent or surface-active agents which are used in the preparation of the graft copolymer according to the invention constitute an integral part of the invention. It is known in polysaccharide chemistry that surfactants tend to react with the polysaccharides (some more than others) so that the dispersibility of the polysaccharide in water is reduced by the presence of a surfactant (see e.g. Gray, Virginia M., et al., Die Starke, 14, pp. 239-246 [1962]). The polysaccharide and the surfactant form a complex which decreases the dispersibility of the polysaccharide in water compared to the dispersibility without the surfactant. In the absence of the surfactant, the beads of the graft product coagulate during the polymerization, the suspension characteristics of the reaction mixture being abolished and the polymer being made difficult to handle.
Im allgemeinen können beliebige Arten von grenzflächenaktiven Mitteln, z. B. nichtionische, anionische oder kationische, bei der Verwirklichung der Erfindung verwendet werden, wobei anionische und nichtionische grenzflächenaktive Mittel bevorzugt werden. Besonders geeignete grenzflächenaktive Mittel stellen öllösliche polyhydroxyäthylierte Verbindungen, bekannt als nichtionische grenzflächenaktive Mittel, z. B. hydroxyäthylierte Nonylphenole, hydroxyäthylierte langkettige Monocarbonsäuren und -fettsäuren, Fettsäureester des Sorbits und hydroxyäthylierte Fettsäureester des Sorbits dar. Die gewöhnlich eingesetzten aktiven kationischen und aktiven anionischen Emulgatoren, wie Alkylarylsulfonate, lineare Alkylsulfonate und -sulfate, z. B. Laurylsulfat oder Sulfobernsteinsäureester, können ebenfalls, wenn gewünscht, anstelle von Substanzen des nichtionischen Typs oder in Vermischung mit diesen Substanzen verwendet werden.In general, any type of surfactant, e.g. Nonionic, anionic or cationic, can be used in practicing the invention, with anionic and nonionic surfactants being preferred. Particularly suitable surfactants are oil-soluble polyhydroxyethylated compounds known as nonionic surfactants, e.g. B. hydroxyethylated nonylphenols, hydroxyethylated long-chain monocarboxylic acids and fatty acids, fatty acid esters of sorbitol and hydroxyethylated fatty acid esters of sorbitol. B. lauryl sulfate or sulfosuccinic acid esters can also be used in place of or in admixture with substances of the nonionic type, if desired.
Derartige geeignete grenzflächenaktive Mittel sind insbesondere die im Handel erhältlichen folgenden Produkte: eine 30%ige wäßrige Lösung von Natriumdodecylbenzolsulfonat, Sorbitanmonostearat (wachsartiger Feststoff bei 25°, spezifisches Gewicht: 0,98-1,03 g/ml und Flammp.: 232°C), Sorbitanmonooleat (ölige Flüssigkeit bei 25°C, spezifisches Gewicht: 1,00 bis 1,05 g/ml, Flammp.: 210°C), Nonylphenoxypoly(äthylenoxy)äthanol (nichtionisches grenzflächenaktives Mittel, wachsartig, 100%ige Konzentration, hydrophil-lipophiles Gleichgewicht: 19,0) und Octylphenoxypolyäthoxyäthanol (nichtionisches grenzflächenaktives Mittel in flüssiger Form und 70%iger Konzentration, hydrophil-lipophiles Gleichgewicht: 17,9).Suitable surface-active agents of this type are in particular the following commercially available products: a 30% strength aqueous solution of sodium dodecylbenzenesulfonate, sorbitan monostearate (waxy solid at 25 °, specific weight: 0.98-1.03 g / ml and flame point: 232 ° C ), Sorbitan monooleate (oily liquid at 25 ° C, specific weight: 1.00 to 1.05 g / ml, flame point: 210 ° C), nonylphenoxypoly (ethyleneoxy) ethanol (non-ionic surface-active agent, waxy, 100% concentration, hydrophilic-lipophilic balance: 19.0) and octylphenoxypolyethoxyethanol (non-ionic surface-active agent in liquid form and 70% concentration, hydrophilic-lipophilic balance: 17.9).
Die Brauchbarkeit besonderer grenzflächenaktiver Mittel bei der Verwirklichung der Erfindung kann leicht dadurch ermittelt werden, daß eine aliquote Menge der vorgesehenen Mischung hergestellt wird, um festzustellen, ob eine stabile Suspension gebildet wird. Insbesondere hängt jedoch die Wahl des besonderen grenzflächenaktiven Mittels (oder besonderen grenzflächenaktiven Mitteln), die eingesetzt werden sollen, von einer Anzahl von Faktoren ab, wie von der Art der kontinuierlichen Phase, dem Verhältnis des Polysaccharids zu dem wasserlöslichen Monomer, dem Monomer (oder den Monomeren), das zur Herstellung des Pfropfproduktes verwendet wird, der Konzentration des (der) Monomers (Monomeren) in der wäßrigen Phase, der Art des eingesetzten Polymerisationssubstrats und den pH-Bedingungen, unter denen die Polymerisationsreaktion abläuft. Wenn ein wasserlösliches grenzflächenaktives Mittel verwendet wird, wird dieses der wäßrigen Phase einverleibt und in Mengen von 0,5 bis 12 Gew.-%, bezogen auf das Polysaccharidsubstrat, verwendet. Wenn ein lösungsmittellösliches grenzflächenaktives Mittel verwendet wird, wird es der homogenen Phase in Mengen von 1 bis 12 Gew.-%, bezogen auf das Lösungsmittel, einverleibt. Wenn beide Arten von grenzflächenaktiven Mitteln zur Anwendung kommen, werden sie im allgemeinen innerhalb der gleichen Konzentrationsbereiche, die oben bereits erwähnt wurden, den jeweiligen Phasen zugegeben.The utility of particular surfactants in practicing the invention can readily be determined by making an aliquot of the intended mixture to determine whether a stable suspension is formed. In particular, however, the choice of the particular surfactant (or surfactants) to be employed will depend on a number of factors, such as the type of continuous phase, the ratio of the polysaccharide to the water-soluble monomer, the monomer (or s) Monomers) used to prepare the graft product, the concentration of the monomer (s) in the aqueous phase, the type of polymerization substrate used and the pH conditions under which the polymerization reaction takes place. When a water-soluble surfactant is used, it is incorporated into the aqueous phase and used in amounts of from 0.5 to 12% by weight based on the polysaccharide substrate. When a solvent-soluble surfactant is used, it is incorporated into the homogeneous phase in amounts of 1 to 12% by weight based on the solvent. When both types of surfactants are used, they are generally added to the respective phases within the same concentration ranges as mentioned above.
Andere Additive, die herkömmlicherweise bei der Pfropfpolymerisationsreaktion verwendet werden, werden im allgemeinen zu der wäßrigen Monomerlösung gegeben. Wenn daher Puffer zur Einregulierung des pH-Wertes erforderlich sind, so z. B. in dem Fall, in dem ein anionisches Monomer oder eine Mischung aus anionischen und kationischen Monomeren eingesetzt wird, sollten derartige Puffer zu der wäßrigen Monomerlösung gegeben werden.Other additives conventionally used in the graft polymerization reaction are generally added to the aqueous monomer solution. Therefore, if buffers are required to regulate the pH, so z. B. in the case in which an anionic monomer or a mixture of anionic and cationic monomers is used, such buffers should be added to the aqueous monomer solution.
Entsprechend einer typischen Pfropfmischpolymerisationsreaktion werden die Monomerlösung, die PoIysaccharidsuspension und der Katalysator zusammen mit irgendwelchen zusätzlichen Bestandteilen in einem Behälter in Kombination eingesetzt, wobei dieser Behälter mit Rührvorrichtungen versehen ist und eine inerte Atmosphäre, die z. B. durch Abziehen der Luft mittels Stickstoff geschaffen wird, einschließt. Die Reihenfolge der Zugabe der einzelnen Bestandteile ist nicht entscheidend. Jedoch sollten beide Phasen im wesentlichen bei der Kombination Raumtemperatur haben. Die Polymerisationsreaktion ist nicht auf eine "Einzelchargen"-Technik beschränkt. Vielmehr kann die Kombination der bei der Reaktion eingesetzten Bestandteile vielfältige Variationen erfahren. Zum Beispiel können die Monomerlösung und eine gesonderte wäßrige Lösung des Katalysators jeweils der Polysaccharidsuspension langsam beigegeben werden (gewöhnlich über eine Zeitdauer von 15 bis 60 Minuten). Gleichermaßen kann die den Katalysator enthaltende Monomerlösung langsam zu der Polysaccharidsuspension gegeben werden.According to a typical graft copolymerization reaction, the monomer solution, the polysaccharide suspension and the catalyst are used together with any additional ingredients in a container in combination, which container is provided with stirring devices and an inert atmosphere, e.g. B. by evacuating the air is created by means of nitrogen. The order in which the individual components are added is not critical. However, both phases should essentially be room temperature when combined. The polymerization reaction is not limited to a "single batch" technique. Rather, the combination of the constituents used in the reaction can experience many variations. For example, the monomer solution and a separate aqueous solution of the catalyst can each be slowly added to the polysaccharide suspension (usually over a period of 15 to 60 minutes). Likewise, the monomer solution containing the catalyst can be slowly added to the polysaccharide suspension.
Die Konzentration des (der) Monomers (Monomeren) des Substrats, der (des) Puffer(s) und des Katalysators in der wäßrigen Phase wird auf den Bereich von 50 bis 90 Gew.-%, vorzugsweise 60 bis 80 Gew.-%, Feststoffe durch Verändern der zur Herstellung der Lösung verwendeten Wassermenge ausgelegt. Die Konzentration des "Polymerisats" (d. h. des Substrats und Monomers) in der kontinuierlichen Phase wird auf 15 bis 50 Gew.-% Feststoffe durch Einregulierung der Menge des organischen Lösungsmittels eingestellt. Die Reaktionsmischung wird von Luft befreit und auf eine geeignete Temperatur (zwischen etwa 40 und 100°C) zur Einleitung der Polymerisation erhitzt. Die Polymerisation wird bei erhöhter Temperatur unter Rühren so lange fortgeführt, bis der angestrebte Umsatz erreicht und das Aufpfropfen vollzogen ist (gewöhnlich nach 1/2 bis 6 Stunden, was von der Art des Initiierens abhängt). Am Ende dieser Periode werden die Kügelchen von der kontinuierlichen Phase abfiltriert (wenn gewünscht, mit einem inerten Lösungsmittel gewaschen) und getrocknet. Das Trocknen kann nach herkömmlichen Verfahren erfolgen, z. B. unter Anwendung eines Vakuumtrockners, eines Wirbelschichttrockners oder eines Walzentrockners. Nach der Filtration kann das Filtrat ohne weiteres in die nächste Polymerisationscharge rückgeführt werden.The concentration of the monomer (s) of the substrate, the buffer (s) and the catalyst in the aqueous phase is set to the range from 50 to 90% by weight, preferably 60 to 80% by weight, Solids designed by changing the amount of water used to make the solution. The concentration of the "polymer" (i.e., substrate and monomer) in the continuous phase is adjusted to 15 to 50 weight percent solids by adjusting the amount of the organic solvent. The reaction mixture is freed from air and heated to a suitable temperature (between about 40 and 100 ° C.) to initiate the polymerization. The polymerization is continued at elevated temperature with stirring until the desired conversion has been reached and grafting is complete (usually after 1/2 to 6 hours, depending on the type of initiation). At the end of this period, the beads are filtered off from the continuous phase (washed with an inert solvent if desired) and dried. Drying can be done by conventional methods, e.g. B. using a vacuum dryer, a fluidized bed dryer or a drum dryer. After the filtration, the filtrate can easily be returned to the next polymerization charge.
Die erfindungsgemäßen Pfropfmischpolymerisate unterscheiden sich in verschiedener Hinsicht von den bekannten Pfropfmischpolymerisaten, was vorrangig auf das hohe Ausmaß des Aufpfropfens und die hohe Umsetzung des Substrats bei der Herstellung zurückgeht.The graft copolymers according to the invention differ in several respects from the known graft copolymers, which is primarily due to the high degree of grafting and the high conversion of the substrate during production.
Die folgenden Beispiele sollen die Erfindung noch näher erläutern. Darin beziehen sich, sofern nichts anderes gesagt wird, alle Teile auf das Gewicht und alle Temperaturen auf °C.The following examples are intended to explain the invention in more detail. Unless otherwise stated, all parts are based on weight and all temperatures are based on ° C.
Beispiel 1example 1
Dieses Beispiel erläutert die Herstellung eines erfindungsgemäßen Pfropfmischpolymerisats aus Wachsmaisstärke, Acrylamid, Acrylsäure und Dimethyldiallylammoniumchlorid.This example explains the production of a graft copolymer according to the invention from waxy maize starch, acrylamide, acrylic acid and dimethyldiallylammonium chloride.
Ein Reaktionsbehälter in Form eines mit einem mechanischen Rührer, einem Rückflußkühler, einem Thermometer und einem Einlaß für die Zugaben versehenen 2-Liter-RundkoIbens wird mit 590 g eines Petroleumlösungsmittels mit C[tief]8-Isoparaffinen als Hauptbestandteil, Kochpunkt 115,56 bis 141,67°C, 32 g des vorstehend genannten Sorbitanmonooleats und 204,6 g Wachsmaisstärke (Feuchtigkeitsgehalt 12%) einer Fluidität von 80 beschickt.A reaction vessel in the form of a 2 liter round flask equipped with a mechanical stirrer, a reflux condenser, and an inlet for the additions is filled with 590 g of a petroleum solvent with C [deep] 8 isoparaffins as the main component, boiling point 115.56 to 141 , 67 ° C, 32 g of the aforementioned sorbitan monooleate and 204.6 g of waxy maize starch (moisture content 12%) with a fluidity of 80 charged.
In einem gesonderten Behälter wurde eine Monomerlösung durch Mischen von 71,1 g Acrylamid, 9,0 g Acrylsäure, 62,7 g einer 64,1 %igen wäßrigen Lösung des Dimethyldiallylammoniumchlorids, 4,0 g einer 1%igen Tetranatriumäthylendiamintetraessigsäurelösung, 10,0 g linearem Natriumdodecylbenzolsulfonat und 64,8 g Wasser hergestellt. Diese Lösung wurde mittels 9,9 ml 12,6 n-Natriumhydroxid auf den pH-Wert von 8,3 eingestellt.In a separate container, a monomer solution was prepared by mixing 71.1 g of acrylamide, 9.0 g of acrylic acid, 62.7 g of a 64.1% strength aqueous solution of dimethyldiallylammonium chloride, 4.0 g of a 1% strength tetrasodium ethylenediaminetetraacetic acid solution, 10.0 g of linear sodium dodecylbenzenesulfonate and 64.8 g of water. This solution was adjusted to pH 8.3 using 9.9 ml of 12.6 N sodium hydroxide.
Die Monomerlösung wurde über eine Zeitdauer von 1/2 Stunde bei 25°C zu der im Reaktor gerührten Mischung aus Stärke, grenzflächenaktivem Mittel und Lösungsmittel gegeben. Nach der Zugabe bestand die Reaktionsmischung aus kleinen, im Lösungsmittelmedium suspendierten Kügelchen.The monomer solution was added over a period of 1/2 hour at 25 ° C. to the stirred mixture of starch, surfactant and solvent in the reactor. After the addition, the reaction mixture consisted of small beads suspended in the solvent medium.
Eine Lösung mit einem Gehalt von 1,08 g Ammoniumpersulfat, 3,24 g Dinatriumhydrogenphosphat und 15 g Wasser wurde langsam während 1/2 Stunde in den Reaktor gegeben. Die Mischung wurde dann durch wechselndes Evakuieren (200 mm Hg) und durch erneutes Unterdrucksetzen auf Atmosphärendruck unter Verwendung von Stickstoff entlüftet. Unter Beibehaltung eines positiven Stickstoffdrucks wurde die Reaktionsmischung 1 Stunde lang auf 60 bis 65°C erhitzt. Die Polymerisationsreaktion wurde bei 60°C initiiert, was sich durch eine exotherme Reaktion deutlich machte. Die Reaktionsmischung wurde während des exothermen Reaktionsablaufes und danach während zusätzlicher vier Stunden auf 65 bis 70°C gehalten. Mit Ablauf dieser Zeitdauer wurde die Reaktionsmischung abgekühlt. Die Polymerisatkügelchen wurden durch Filtration und Trocknen gewonnen. Das getrocknete Produkt bestand aus fließfähigen, gleichförmigen Kügelchen. Die Ausbeute betrug 320 g mit einem Feststoffgehalt von 95%. Das Polymerisat wurde in Wasser dispergiert (2% Feststoffe), in einem siedenden Wasserbad 20 Minuten lang erhitzt und dann gegen destilliertes Wasser einer Dialyse unterzogen. Nach der Dialyse wurde der Stickstoffgehalt des Polymerisats mit 5,3% und die Grundviskosität mit 1,52 dl/g, gemessen in einer 1 n-KCl-Lösung, ermittelt. Der Monomerumsatz wurde mit 93% und der Aufpfropfungsgrad mit 85% errechnet.A solution containing 1.08 g ammonium persulfate, 3.24 g disodium hydrogen phosphate and 15 g water was slowly added to the reactor over 1/2 hour. The mixture was then alternately evacuated (200 mm Hg) and repressurized to atmospheric pressure using nitrogen. While maintaining a positive nitrogen pressure, the reaction mixture was heated to 60-65 ° C for 1 hour. The polymerization reaction was initiated at 60 ° C., which was made clear by an exothermic reaction. The reaction mixture was kept at 65 to 70 ° C. during the exothermic course of the reaction and then for an additional four hours. At the end of this period, the reaction mixture was cooled. The polymer beads were collected by filtration and drying. The dried product consisted of flowable, uniform beads. The yield was 320 g with a solids content of 95%. The polymer was dispersed in water (2% solids), heated in a boiling water bath for 20 minutes, and then dialyzed against distilled water. After dialysis, the nitrogen content of the polymer was determined to be 5.3% and the basic viscosity to be 1.52 dl / g, measured in a 1N KCl solution. The monomer conversion was calculated to be 93% and the degree of grafting to be 85%.
Beispiele 2 bis 8Examples 2 to 8
Es wurde das Verfahren nach Beispiel 1 durchgeführt, wobei Pfropfmischpolymerisate hergestellt sowie diejenigen Bestandteile und Mengen und Reaktionsbedingungen gewählt bzw. eingehalten wurden, die aus der Tabelle I hervorgehen.The process according to Example 1 was carried out, graft copolymers being prepared and those constituents and amounts and reaction conditions selected or adhered to which emerge from Table I.
Beispiel 9Example 9
Dieses Beispiel erläutert die nützliche Verwendung ausgewählter kationischer Pfropfprodukte, die erfindungsgemäß hergestellt wurden, zur Retention von Pigmenten während des Papierherstellungsverfahrens.This example illustrates the useful use of selected cationic graft products made in accordance with the present invention for retention of pigments during the papermaking process.
Gebleichte Weichholzsulfatcellulose (360 g) wurde so lange in Wasser aufbereitet, bis eine 1,5%ige (Gew./Vol.-)Aufschlämmung eine Entwässerungsneigung von 600 entsprechend der "Canadian Standard Freeness" aufwies. Zu der aufbereiteten Zellstoffaufschlämmung wurden 36 g TiO[tief]2 gegeben und die Wasserhärte auf ppm eingeregelt. Diese derartig hergerichtete Zellstoffaufschlämmung wurde dann auf eine endgültige Konsistenz von 0,5% (Gew./Vol.) des Zellstoffs verdünnt.Bleached softwood sulfate cellulose (360 g) was prepared in water until a 1.5% (w / v) slurry had a drainage tendency of 600 according to the "Canadian Standard Freeness". 36 g of TiO [deep] 2 were added to the prepared pulp slurry and the water hardness was adjusted to ppm. This so prepared pulp slurry was then diluted to a final consistency of 0.5% (w / v) of the pulp.
Es wurde eine ausreichende Menge an Zellstoffaufschlämmung zur Herstellung von 3,5 g eines Blattes (etwa 700 ml) in ein Becherglas gegeben und mit einem mechanischen Rührer gerührt. An diesem Punkt wurde der pH-Wert, wie erforderlich, unter Verwendung von zur Papierherstellung geeigneten Alauns für verschiedene Versuche auf 7,5, 6,0 und 4,5 eingestellt. Die Aufschlämmungen wurden dann mit verdünnten wäßrigen Lösungen in verschiedenen Konzentrationen (wie angegeben) an geeignetem Retentionsmittel behandelt und 30 Sekunden bis zu 1 Minute gemischt.A sufficient amount of pulp slurry to make 3.5 g of a sheet (about 700 ml) was placed in a beaker and stirred with a mechanical stirrer. At this point the pH was adjusted as required using Alum suitable for papermaking was adjusted to 7.5, 6.0 and 4.5 for various experiments. The slurries were then treated with dilute aqueous solutions at various concentrations (as indicated) of suitable retention aid and mixed for 30 seconds to 1 minute.
Die behandelte Aufschlämmung wurde dann in einen in englischsprachigen Ländern als "Noble and Wood head box" bezeichneten Behälter gegeben, der etwa 10 l Wasser enthielt, und dann manuell gemischt. Der Behälter wurde evakuiert und trockengelegt und die Blätter in einer Walzeneinrichtung des zur Herstellung von Fließpapier geeigneten Typs verpreßt und getrocknet. Die in den Blättern zurückgehaltene Menge an Pigmenten wurde mittels einer Isotopentechnik bestimmt und als theoretische prozentuale Menge ausgedrückt.The treated slurry was then placed in a container known in English-speaking countries as a "Noble and Wood head box" containing about 10 liters of water and then mixed manually. The container was evacuated and drained and the sheets pressed and dried in a roller device of the type suitable for making blotter paper. The amount of pigment retained in the leaves was determined by an isotope technique and expressed as a theoretical percentage.
Tabelle ITable I.
Die Versuchsergebnisse mit den zwei Stärkepfropfmischpolymerisaten, die entsprechend der obigen Verfahrensweise hergestellt wurden und als Retentionsmittel bei Konzentrationen von 0,01 und 0,03% Zugabe bei pH-Werten von 7,5 (0% Alaun), 6,0 (4% Alaun) und 4,5 (11% Alaun) getestet wurden, werden in der Tabelle II tabellarisch erfaßt, wobei auf prozentual zurückgehaltenes Pigment abgestellt wird. Das erfindungsgemäße Pfropfmischpolymerisat wird mit einem typischen kommerziell erhältlichen 100%igen synthetischen Retentionsmittel und einem Pfropfmischpolymerisat unter Einsetzung der Zusammensetzung des Beispiels 1, das jedoch nach einer herkömmlichen Pfropfmethode in wäßrigem Medium hergestellt wurde, verglichen.The test results with the two starch graft copolymers, which were prepared according to the above procedure and as retention aids at concentrations of 0.01 and 0.03% addition at pH values of 7.5 (0% alum), 6.0 (4% alum ) and 4.5 (11% alum) were tested, are tabulated in Table II, based on the percentage of pigment retained. The graft copolymer according to the invention is compared with a typical commercially available 100% synthetic retention aid and a graft copolymer employing the composition of Example 1, which, however, was prepared by a conventional grafting method in an aqueous medium.
Beispiel 10Example 10
Dieses Beispiel erläutert die Herstellung eines Pfropfmischpolymerisats aus Wachsmaisstärke und Acrylamid nach dem erfindungsgemäßen Verfahren, wobei ein grenzflächenaktives Mittel lediglich in der Monomerlösung eingesetzt wird.This example explains the production of a graft copolymer from waxy maize starch and acrylamide by the process according to the invention, a surface-active agent being used only in the monomer solution.
Ein Reaktionsbehälter in Form eines 500-ml-Rundkolbens mit Rührer, Thermometer, Kondensator und einem Zugabeeinlaß wurde mit 225 ml Toluol beschickt. Dann wurden 67,8 g Wachsmaisstärke (nicht umgesetzte) mit 12% Feuchtigkeit unter Sieben eingebracht. In einem gesonderten Becher wurde eine Lösung hergestellt, die 15 g Acrylamid in Mischung mit 28,6 g Wasser und 7,5 g kommerziell erhältlichen Natriumlaurylsulfatschuppen enthielt. Diese Lösung wurde langsam über einen Tropftrichter während 15 Minuten zu der Stärkesuspension gegeben. Nach der Zugabe bestand die Reaktionsmischung aus kleinen, in dem Lösungsmittel suspendierten Kügelchen.A reaction vessel in the form of a 500 ml round bottom flask equipped with a stirrer, thermometer, condenser and an addition inlet was charged with 225 ml of toluene. Then 67.8 g of waxy maize starch (unreacted) with 12% moisture were placed under sieves. A solution containing 15 g of acrylamide mixed with 28.6 g of water and 7.5 g of commercially available sodium lauryl sulfate flakes was prepared in a separate beaker. This solution was slowly added to the starch suspension via a dropping funnel over 15 minutes. After the addition, the reaction mixture consisted of small beads suspended in the solvent.
Die Reaktionsmischung wurde durch Einleiten von Stickstoffgas unter das Flüssigkeitsniveau in einer Menge von 50 ml/min während 15 Minuten entlüftet. Am Ende des Durchspülens wurde die Menge an eingeleitetem Stickstoff auf 10 ml/min herabgesetzt. Etwa 3 ml einer 0,5 n-Cerammoniumnitratlösung (in 1 n-NH[tief]4NO[tief]3) wurde zu der Reaktionsmischung mittels einer Spritze gegeben. Die Temperatur der Reaktionsmischung stieg von 25 auf 35°C. Sie wurde mittels eines Eis/Wasser-Bades auf 30 bis 32°C gekühlt. Der exotherme Vorgang dauerte 30 Minuten, wonach die Reaktionsmischung auf 30°C erwärmt und darauf eine zusätzliche Stunde belassen wurde.The reaction mixture was deaerated by introducing nitrogen gas below the liquid level in an amount of 50 ml / min for 15 minutes. At the end of the purging, the amount of nitrogen introduced was reduced to 10 ml / min. About 3 ml of a 0.5N cerium ammonium nitrate solution (in 1N NH [deep] 4NO [deep] 3) was added to the reaction mixture via a syringe. The temperature of the reaction mixture rose from 25 to 35 ° C. It was cooled to 30 to 32 ° C using an ice / water bath. The exothermic process lasted 30 minutes, after which the reaction mixture was warmed to 30 ° C and then left for an additional hour.
Das Pfropfmischpolymerisat wurde quantitativ durch Filtration in Form kleiner, nicht ganz weißer, gleichförmiger Kügelchen gewonnen und 1 Stunde lang bei 60°C getrocknet. Das Copolymerisat wurde in Wasser bei einer Feststoffkonzentration von 2,5% 20 Minuten lang erhitzt und danach bei einem pH-Wert von 7 dialysiert. Der Stickstoffgehalt nach der Dialyse betrug 3,82%, was einen 97%igen Umsatz des Monomers auswies. Das Ausmaß bzw. der Grad des Aufpfropfens wurde mit 81% ermittelt.The graft copolymer was obtained quantitatively by filtration in the form of small, not entirely white, uniform spheres and dried at 60 ° C. for 1 hour. The copolymer was heated in water at a solids concentration of 2.5% for 20 minutes and then dialyzed at pH 7. The nitrogen content after dialysis was 3.82%, which indicated a 97% conversion of the monomer. The extent or degree of grafting was found to be 81%.
Beispiel 11Example 11
Dieses Beispiel erläutert die Herstellung eines Pfropfmischpolymerisats aus Maisstärke einer Fluidität von 50, Acrylamid und Acrylsäure, wobei die Anteile des Monomers und der Katalysatorlösung während einer solchen Zeitdauer langsam zugegeben werden, die einer bevorzugten Ausgestaltung der Erfindung entspricht.This example illustrates the production of a graft copolymer from corn starch with a fluidity of 50, acrylamide and acrylic acid, the proportions of the monomer and the catalyst solution being added slowly over a period of time which corresponds to a preferred embodiment of the invention.
Tabelle IITable II
Ein Ein-Liter-Rundkolben, der mit einem mechanischen Rührer, einem Thermometer, einem Kondensator und einem Ausgleichstropftrichter geeigneter Größe versehen war, wurde mit 200 g Isoparaffinlösungsmittel (s. Tabelle I), 20 g Sorbitanmonooleat (vorstehend spezifiziert) und 45,5 g Maisstärke einer Fluidität von 50 und eines Wassergehaltes von 12% beschickt.A one liter round bottom flask fitted with a mechanical stirrer, thermometer, condenser, and appropriately sized equalizing dropping funnel was charged with 200 grams of isoparaffin solvent (see Table I), 20 grams of sorbitan monooleate (specified above), and 45.5 grams Corn starch charged with a fluidity of 50 and a water content of 12%.
In einem gesonderten Becher wurde eine Monomerlösung hergestellt, die 52,2 g Acrylamid, 7,8 g Acrylsäure, 25 g einer 20%igen wäßrigen Lösung von Natriumdodecylbenzolsulfonat und 10,1 g Wasser enthielt. Der pH-Wert der Monomerlösung wurde auf 8,3 mittels 18,2 n-NaOH eingestellt.A monomer solution containing 52.2 g of acrylamide, 7.8 g of acrylic acid, 25 g of a 20% strength aqueous solution of sodium dodecylbenzenesulfonate and 10.1 g of water was prepared in a separate beaker. The pH of the monomer solution was adjusted to 8.3 using 18.2 N NaOH.
Eine Katalysatorlösung wurde durch Mischen von 0,25 g Ammoniumpersulfat, 0,75 g Dinatriumhydrogenphosphat und 10,0 g Wasser hergestellt. Zu dem die Stärkesuspension enthaltenden Kolben wurden jeweils 25% der Monomerlösung und der Katalysatorlösung gegeben. Der Reaktionskolben wurde anschließend unter Vakuum und unter Einsatz von Stickstoff entlüftet und auf 65 bis 70°C erhitzt. Bei dieser Temperatur wurden die verbleibenden Anteile jeder Lösung langsam während einer Zeitdauer von 2 Stunden zugegeben, wonach die Reaktionsmischung zusätzliche 2 Stunden erhitzt wurde. Das Mischpolymerisat wurde mittels Filtration in Form kleiner gleichförmiger Kügelchen isoliert.A catalyst solution was prepared by mixing 0.25 g ammonium persulfate, 0.75 g disodium hydrogen phosphate and 10.0 g water. 25% each of the monomer solution and the catalyst solution were added to the flask containing the starch suspension. The reaction flask was then vented under vacuum using nitrogen and heated to 65-70 ° C. At this temperature the remaining portions of each solution were slowly added over a 2 hour period after which the reaction mixture was heated an additional 2 hours. The copolymer was isolated in the form of small, uniform spheres by means of filtration.
Eine 1 %ige Lösung des Polymerisats in Wasser zeigte eine Viskosität von 300 cP und hatte einen Stickstoffgehalt von 9,8% (nach der Dialyse), was einen 95%igen Monomerumsatz nachwies.A 1% solution of the polymer in water had a viscosity of 300 cP and a nitrogen content of 9.8% (after dialysis), which showed a 95% monomer conversion.
Beispiele 12 bis 17Examples 12-17
Es wurden Pfropfmischpolymerisate hergestellt, indem die Bestandteile und die Bedingungen, wie aus der Tabelle III ersichtlich, eingesetzt bzw. gewählt wurden und das auf langsamer Zugabe basierende Verfahren, im wesentlichen wie das in Beispiel 11 beschriebene, durchgeführt wurde.Graft copolymers were prepared by employing or choosing the ingredients and conditions as shown in Table III and performing the slow addition process essentially as that described in Example 11.
Beispiel 18Example 18
Unter Anwendung des auf der langsamen Zugabe basierenden Verfahrens, im wesentlichen wie das in Beispiel 11 beschriebene, wurde ein Cellulose-(g)-Acrylamid-Mischpolymerisat (Acrylamid-Monomer auf Cellulose aufgepfropft) hergestellt und ohne Isolieren nachfolgend teilweise mittels Natriumhydroxid hydrolysiert, um eine Carbonsäure-Funktionalität einzuführen.Using the slow addition method essentially as that described in Example 11, a cellulose (g) acrylamide copolymer (acrylamide monomer grafted onto cellulose) was prepared and subsequently partially hydrolyzed with sodium hydroxide without isolation to give a Introduce carboxylic acid functionality.
Die Polysaccharidsuspension enthielt 42 g kleines Alpha-Cellulosepulver, 200 g einer hochreinen Mischung von Isoparaffinen (mit einem Gehalt an verzweigten aliphatischen C[tief]10-, C[tief]11-, und C[tief]12-Kohlenwasserstoffen, wobei der Hauptbestandteil C[tief]10-Kohlenwasserstoffe sind, und einem Siedepunkt von 159 bis 174°C) und 20 g vorstehend spezifiziertes Sorbitanmonooleat.The polysaccharide suspension contained 42 g of small alpha cellulose powder, 200 g of a highly pure mixture of isoparaffins (containing branched aliphatic C [deep] 10, C [deep] 11, and C [deep] 12 hydrocarbons, the main component being C [deep] 10 hydrocarbons, and a boiling point of 159 to 174 ° C) and 20 g of the sorbitan monooleate specified above.
Die Monomerlösung wurde derartig hergestellt, daß sie 60 g Acrylamid, 9,9 g Wasser und 25 g Natriumdodecylbenzolsulfonat (20%ige wäßrige Lösung) enthielt. Die gepufferte Katalysatorlösung enthielt 0,25 g Ammoniumpersulfat, 0,75 g Na[tief]2HPO[tief]4 und 10,0 g Wasser.The monomer solution was prepared to contain 60 g of acrylamide, 9.9 g of water and 25 g of sodium dodecylbenzenesulfonate (20% aqueous solution). The buffered catalyst solution contained 0.25 g ammonium persulfate, 0.75 g Na [deep] 2HPO [deep] 4 and 10.0 g water.
Wie in Beispiel 11 wurden zunächst jeweils 25% der Monomerlösung und der Katalysatorlösung anfänglich zu dem Reaktionskolben, der die Polysaccharidsuspension enthielt, gegeben.As in Example 11, 25% each of the monomer solution and the catalyst solution were initially added to the reaction flask containing the polysaccharide suspension.
Tabelle IIITable III
Das Verfahren des Beispiels 11 folgte, um das fertige Mischpolymerisat als Zwischenprodukt nach etwa 4stündiger Reaktionszeit herzustellen. Nach der Polymerisation wurden langsam zu der heißen Mischung (65 bis 70°C) während 1 Stunde 24,0 ml 18,2 n-Natriumhydroxid hinzugegeben. Die Hydrolyse wurde weitere 2 Stunden unter Aufrechterhaltung der Temperatur von 65 bis 70°C fortgeführt. Das hydrolysierte Mischpolymerisat wurde danach in Form gleichförmiger, feiner, nicht ganz weißer Kügelchen mittels Filtration isoliert, gewaschen und getrocknet.The procedure of Example 11 was followed to produce the finished copolymer as an intermediate after about 4 hours of reaction time. After the polymerization, 24.0 ml of 18.2 N sodium hydroxide were slowly added to the hot mixture (65 to 70 ° C.) over 1 hour. The hydrolysis was continued for a further 2 hours while maintaining the temperature at 65 to 70 ° C. The hydrolyzed copolymer was then isolated in the form of uniform, fine, not entirely white spheres by means of filtration, washed and dried.
Nach dem erfindungsgemäßen Verfahren werden im Ergebnis stark substituierte Pfropfmischpolymerisate von Polysacchariden bereitgestellt, wobei ein 2-Phasenreaktionssystem und kontrollierte Bedingungen gewählt bzw. eingehalten werden. Das Verfahren vermittelt wasserlöslichen Monomeren eine starke Aufpfropfwirksamkeit auf Polysaccharidsubstrate und führt zu hoch umgesetzten Pfropfmischpolymerisaten, die nach bekannten Verfahren nicht erhältlich sind.The result of the process according to the invention is to provide highly substituted graft copolymers of polysaccharides, a 2-phase reaction system and controlled conditions being selected or adhered to. The process gives water-soluble monomers a strong grafting effectiveness onto polysaccharide substrates and leads to highly converted graft copolymers which are not obtainable by known processes.
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US05/860,951 US4131576A (en) | 1977-12-15 | 1977-12-15 | Process for the preparation of graft copolymers of a water soluble monomer and polysaccharide employing a two-phase reaction system |
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DE2840010B2 DE2840010B2 (en) | 1981-07-16 |
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JP (1) | JPS5483987A (en) |
BE (1) | BE870955A (en) |
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DE (1) | DE2840010C3 (en) |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1736508A1 (en) | 2005-06-22 | 2006-12-27 | Basf Aktiengesellschaft | Hydrogel-forming polymers with increased permeability and high absorption capacity |
EP2345431A2 (en) | 2002-06-11 | 2011-07-20 | Basf Se | Method for producing esters from polyalcohols |
Families Citing this family (706)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10130427A1 (en) | 2001-06-23 | 2003-03-27 | Reinmar Peppmoeller | Stable, water-swellable and absorbent anionic polymers with a sponge structure and their production and use |
US4803071A (en) * | 1980-02-11 | 1989-02-07 | National Starch And Chemical Corporation | Hair care compositions |
US4375535A (en) * | 1980-04-28 | 1983-03-01 | Standard Brands Incorporated | Stable liquid, amylopectin starch graft copolymer compositions |
IT1140999B (en) * | 1980-06-18 | 1986-10-10 | Italfarmaco Spa | MODIFIED GLYCOSAMINOGLICANS EQUIPPED WITH ANTI-LIPEMIC ACTIVITY AND WITHOUT ANTI-COAGULANT ACTIVITY |
LU83350A1 (en) * | 1981-05-08 | 1983-03-24 | Oreal | COMPOSITION FOR THE TREATMENT OF KERATINIC FIBERS BASED ON CATIONIC POLYMER AND ANIONIC POLYMER HAVING VINYLSULFONIC GROUPS AND METHOD OF TREATING THE SAME |
JPS5832641A (en) * | 1981-08-20 | 1983-02-25 | Kao Corp | Water-absorbing composition |
US4517351A (en) * | 1982-08-11 | 1985-05-14 | National Starch And Chemical Corporation | Process for reacting quaternary ammonium monomer in the presence of anionic polymers |
US4464523A (en) * | 1983-05-16 | 1984-08-07 | National Starch And Chemical Corporation | Process for the preparation of graft copolymers of cellulose derivatives and diallyl, dialkyl ammonium halides |
US4684708A (en) * | 1985-03-11 | 1987-08-04 | Akzo N.V. | Cationic grafted starch copolymers |
DE3518464A1 (en) * | 1985-05-23 | 1986-11-27 | Hüls AG, 4370 Marl | METHOD FOR PRODUCING LOW-VISCOSE STARCH DISPERSIONS |
US4690996A (en) * | 1985-08-28 | 1987-09-01 | National Starch And Chemical Corporation | Inverse emulsions |
GB8602649D0 (en) * | 1986-02-04 | 1986-03-12 | Allied Colloids Ltd | Polymers |
LU86429A1 (en) * | 1986-05-16 | 1987-12-16 | Oreal | COSMETIC COMPOSITIONS CONTAINING A CATIONIC POLYMER AND AN ANIONIC POLYMER AS A THICKENING AGENT |
US4737156A (en) * | 1986-10-27 | 1988-04-12 | National Starch And Chemical Corporation | Fabric treatment with a composition comprising a cellulose graft copolymer |
US5132284A (en) * | 1988-04-26 | 1992-07-21 | National Starch And Chemical Investment Holding Corporation | Polyamphoteric polysaccharide graft copolymers neutrally charged |
GB8820332D0 (en) * | 1988-08-26 | 1988-09-28 | Allied Colloids Ltd | Graft copolymers |
US4973641A (en) * | 1988-11-18 | 1990-11-27 | National Starch And Chemical Investment Holding Corporation | Polysaccharide graft copolymers containing reactive aminoethyl halide group |
DE69021044T2 (en) * | 1989-01-24 | 1996-02-08 | Dow Chemical Co | AGGREGATES OR CLUSTERS OF WATER SWELLABLE POLYMERS WITH INCREASED HYDRATION SPEED COMPARED TO NON-ASSOCIATED WATER SWELLABLE POLYMERS. |
US5067565A (en) * | 1989-03-10 | 1991-11-26 | Halliburton Company | Crosslinkable cellulose derivatives |
US4982793A (en) * | 1989-03-10 | 1991-01-08 | Halliburton Company | Crosslinkable cellulose derivatives |
DE4014628A1 (en) * | 1990-05-08 | 1991-11-14 | Starchem Gmbh | METHOD FOR PRODUCING FINE-PARTICULATED, WATER-SWELLABLE POLYSACCHARIDE GRAFT POLYMERS |
FR2663940B1 (en) * | 1990-07-02 | 1994-04-08 | Rhone Poulenc Chimie | GRAFT POLYSACCHARIDES, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS SEQUESTRATION AGENTS. |
DE4034882A1 (en) * | 1990-11-02 | 1992-05-07 | Starchem Gmbh | METHOD FOR PRODUCING FINE-PARTICULATED, WATER-SWELLABLE POLYSACCHARIDE GRAFT POLYMERS |
DE4105000A1 (en) * | 1991-02-19 | 1992-08-20 | Starchem Gmbh | METHOD FOR PRODUCING FINE-PARTICULATED, WATER-SWELLABLE POLYSACCHARIDE GRAFT POLYMERS |
NZ243274A (en) * | 1991-06-28 | 1994-12-22 | Calgon Corp | Hair care compositions containing ampholytic terpolymers |
CA2072185C (en) * | 1991-06-28 | 2002-10-01 | Shih-Ruey T. Chen | Ampholyte terpolymers providing superior conditioning properties in shampoos and other hair care products |
CA2072175A1 (en) * | 1991-06-28 | 1992-12-29 | Shih-Ruey T. Chen | Ampholyte terpolymers providing superior conditioning properties in shampoos and other hair care products |
DE4125752A1 (en) * | 1991-08-03 | 1993-02-04 | Basf Ag | POLYMERISATES FROM ETHYLENICALLY UNSATURATED, N-CONTAINING COMPOUNDS, POLYMERIZED IN THE PRESENCE OF MONOSACCHARIDES, OLIGOSACCHARIDES, POLYSACCHARIDES OR THEIR DERIVATIVES |
US5338541A (en) * | 1992-10-15 | 1994-08-16 | Calgon Corporation | Dual cationic terpolymers providing superior conditioning properties in hair, skin and nail care products |
DE4244548C2 (en) | 1992-12-30 | 1997-10-02 | Stockhausen Chem Fab Gmbh | Powdery liquids under load as well as blood-absorbing polymers, processes for their production and their use in textile constructions for personal hygiene |
US6451121B2 (en) | 1993-07-30 | 2002-09-17 | National Starch And Chemical Investment Holding Corporation | Thermally-inhibited non-pregelatinized granular starches and flours and process for their preparation |
FR2718961B1 (en) * | 1994-04-22 | 1996-06-21 | Oreal | Compositions for washing and treating hair and skin based on ceramide and polymers with cationic groups. |
EP0774491A3 (en) | 1995-11-20 | 1997-12-03 | General Electric Company | Films, sheets and molded products made of a polyester/polycarbonate composition |
FR2749506B1 (en) | 1996-06-07 | 1998-08-07 | Oreal | DETERGENT COSMETIC COMPOSITIONS FOR HAIR USE AND USE |
JP2000514007A (en) | 1996-07-06 | 2000-10-24 | シュトックハウゼン・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング・ウント・コムパニー・カーゲー | Absorbent insert, method of manufacturing it and its use |
FR2751532B1 (en) * | 1996-07-23 | 1998-08-28 | Oreal | WASHING AND CONDITIONING COMPOSITIONS BASED ON SILICONE AND DIALKYLETHER |
FR2773069B1 (en) | 1997-12-29 | 2001-02-02 | Oreal | COSMETIC COMPOSITION COMPRISING AT LEAST ONE AMIDOETHERCARBOXYLIC ACID SURFACTANT AND AT LEAST ONE ASSOCIATION OF AN ANIONIC POLYMER AND A CATIONIC POLYMER |
US6090884A (en) * | 1998-05-07 | 2000-07-18 | S. C. Johnson Commercial Markets, Inc. | Starch degradation/graft polymerization composition, process, and uses thereof |
FR2785182B1 (en) * | 1998-11-03 | 2002-04-12 | Oreal | PUMP BOTTLE DEVICE CONTAINING A POLYCONDENSATE COMPRISING AT LEAST ONE POLYURETHANE AND / OR POLYUREA PATTERN |
DE19854573A1 (en) | 1998-11-26 | 2000-05-31 | Basf Ag | Process for post-crosslinking hydrogels with 2-oxo-tetrahydro-1,3-oxazines |
DE19903979C2 (en) | 1999-01-25 | 2000-12-21 | Worlee Chemie G M B H | Starch-based graft polymer, process for its production and its use in printing inks over overprint varnishes |
FR2788974B1 (en) | 1999-01-29 | 2001-03-30 | Oreal | KERATINIC FIBER DECOLORING ANHYDROUS COMPOSITION COMPRISING THE ASSOCIATION OF ANIONIC AND / OR NON-IONIC AMPHIPHILIC POLYMERS COMPRISING AT LEAST ONE FATTY CHAIN AND CATIONIC OR AMPHOTERIC SUBSTANTIVE POLYMERS |
FR2788975B1 (en) | 1999-01-29 | 2002-08-09 | Oreal | AQUEOUS READY-TO-USE KERATIN FIBER DECOLORING COMPOSITION COMPRISING THE ASSOCIATION OF A WATER-SOLUBLE SOLVENT AND A NON-IONIC OR ANIONIC AMPHIPHILIC POLYMER COMPRISING AT LEAST ONE FAT CHAIN |
FR2788976B1 (en) | 1999-01-29 | 2003-05-30 | Oreal | KERATIN FIBER DECOLORING ANHYDROUS COMPOSITION COMPRISING THE ASSOCIATION OF A WATER-SOLUBLE THICKENING POLYMER AND A NON-IONIC AMPHIPHILIC POLYMER COMPRISING AT LEAST ONE FAT CHAIN |
FR2788972B1 (en) | 1999-02-03 | 2001-04-13 | Oreal | HAIR COMPOSITION COMPRISING A WASHING BASE, A CATIONIC POLYMER AND AN ANIONIC POLYURETHANE AND USE THEREOF |
FR2788973B1 (en) | 1999-02-03 | 2002-04-05 | Oreal | COSMETIC COMPOSITION COMPRISING AN ANIONIC SURFACTANT, AN AMPHOTERIC SURFACTANT, A POLYOLEFIN OIL, A CATIONIC POLYMER AND A WATER-SOLUBLE SALT OR ALCOHOL, USE AND METHOD |
FR2795310B1 (en) | 1999-06-25 | 2003-02-14 | Oreal | COSMETIC COMPOSITIONS CONTAINING AN AMPHOTERIC POLYMER AND A FIXING / CONDITIONING POLYMER AND USES THEREOF |
FR2795316B1 (en) | 1999-06-28 | 2004-12-24 | Oreal | PERMANENT PROCESS COMPRISING THE PRELIMINARY APPLICATION OF A COMPOSITION COMPRISING AT LEAST ONE ANIONIC POLYMER |
FR2795635B1 (en) | 1999-06-30 | 2006-09-15 | Oreal | MASCARA COMPRISING FILMOGENIC POLYMERS |
FR2795634A1 (en) | 1999-06-30 | 2001-01-05 | Oreal | MASCARA COMPRISING FILM-FORMING POLYMERS |
FR2799971B1 (en) | 1999-10-20 | 2001-12-07 | Oreal | COSMETIC COMPOSITIONS CONTAINING A VINYLDIMETHICONE / DIMETHICONE COPOLYMER AND A CATIONIC POLYMER AND USES THEREOF |
JP4322376B2 (en) | 1999-11-26 | 2009-08-26 | Sabicイノベーティブプラスチックスジャパン合同会社 | Flame retardant resin composition and molded product thereof |
FR2802089B1 (en) | 1999-12-08 | 2002-01-18 | Oreal | COMPOSITION OF OXIDIZING DYE FOR KERANITIC FIBERS INCLUDING A THICKENING POLYMER WITH AMINOPLASTE-ETHER SKELETON |
FR2802092B1 (en) | 1999-12-08 | 2002-01-18 | Oreal | DECOLORING COMPOSITION FOR KERATINIC FIBERS COMPRISING A THICKENER POLYMER WITH AMINOPLASTE-ETHER SKELETON |
FR2802094B1 (en) | 1999-12-13 | 2002-01-18 | Oreal | DECOLORING COMPOSITION FOR KERATINIC FIBERS COMPRISING A COMBINATION OF TWO POLYURETHANE POLYETHERS |
FR2803197B1 (en) | 1999-12-30 | 2002-03-15 | Oreal | COMPOSITION FOR OXIDATION DYEING OF KERATINIC FIBERS COMPRISING A THICKENING POLYMER COMPRISING AT LEAST ONE FATTY CHAIN AND A FATTY ALCOHOL HAVING MORE THAN TWENTY CARBON ATOMS |
FR2803196B1 (en) | 1999-12-30 | 2002-03-15 | Oreal | COMPOSITION FOR THE OXIDATION DYE OF KERATINIC FIBERS COMPRISING A FATTY ALCOHOL HAVING MORE THAN TWENTY CARBON ATOMS AND A NON-IONIC HLB OXYALKYLENE SURFACTANT HIGHER THAN 5 |
FR2803195B1 (en) * | 1999-12-30 | 2002-03-15 | Oreal | COMPOSITION FOR OXIDATION DYEING OF KERATINIC FIBERS COMPRISING A THICKENING POLYMER COMPRISING AT LEAST ONE FATTY CHAIN AND A SINGLE- OR POLY-GLYCEROLE FATTY ALCOHOL |
FR2806274B1 (en) | 2000-03-14 | 2002-09-20 | Oreal | BALL APPLICATOR CONTAINING A HAIR COMPOSITION |
FR2811886B1 (en) | 2000-07-18 | 2003-01-31 | Oreal | HAIR STYLING COMPOSITION ALLOWING HAIR REMODELING AND HAIR REMODELING METHOD USING SUCH COMPOSITION |
FR2812810B1 (en) | 2000-08-11 | 2002-10-11 | Oreal | COMPOSITION FOR OXIDATION DYEING OF KERATINIC FIBERS COMPRISING A CATIONIC AMPHIPHILIC POLYMER, OXYALKYLENE OR POLYGLYCEROLE FATTY ALCOHOL AND HYDROXYL SOLVENT |
WO2002013772A2 (en) | 2000-08-16 | 2002-02-21 | L'oreal | Hair styling composition comprising adhesive particles |
EP1311229A2 (en) * | 2000-08-16 | 2003-05-21 | L'oreal | Hair styling composition comprising encapsulated adhesives |
FR2813016B1 (en) * | 2000-08-21 | 2002-10-11 | Oreal | COLORING COMPOSITION FOR DYED KERATINIC FIBERS |
CA2354836A1 (en) * | 2000-08-25 | 2002-02-25 | L'oreal S.A. | Protection of keratinous fibers using ceramides and/or glycoceramides |
DE10043710B4 (en) | 2000-09-04 | 2015-01-15 | Evonik Degussa Gmbh | Use of powdery postcrosslinked polymers and hygiene articles |
US6787574B1 (en) | 2000-10-24 | 2004-09-07 | Georgia-Pacific Resins, Inc. | Emulsification of alkenyl succinic anhydride size |
FR2815853B1 (en) * | 2000-10-27 | 2002-12-27 | Oreal | HAIR COSMETIC COMPOSITION IN THE FORM OF FOAM COMPRISING AT LEAST ONE THICKENER POLYMER WITH AMINOPLASTE-ETHER SKELETON |
FR2816207B1 (en) * | 2000-11-08 | 2003-01-03 | Oreal | COMPOSITION OF OXIDIZING DYE FOR KERATINIC FIBERS CONTAINING A CATIONIC ASSOCIATIVE POLYURETHANE |
FR2816209B1 (en) * | 2000-11-08 | 2005-02-25 | Oreal | DECOLORATION COMPOSITION FOR KERATIN FIBERS COMPRISING A CATIONIC ASSOCIATIVE POLYURETHANE |
FR2816208B1 (en) * | 2000-11-08 | 2003-01-03 | Oreal | DIRECT DYE COMPOSITION FOR KERATINIC FIBERS COMPRISING A CATIONIC ASSOCIATIVE POLYURETHANE |
FR2816210B1 (en) * | 2000-11-08 | 2005-02-25 | Oreal | COMPOSITION FOR THE PERMANENT DECOLORATION OR DEFORMATION OF KERATIN FIBERS COMPRISING A CATIONIC ASSOCIATIVE POLYURETHANE |
FR2816834B1 (en) * | 2000-11-20 | 2005-06-24 | Oreal | KERATINIC FIBER TREATMENT COMPOSITION CONSISTING OF A CATIONIC ASSOCIATIVE POLYURETHANE POLYMER AND A PROTECTIVE OR CONDITIONER |
FR2817466B1 (en) * | 2000-12-04 | 2004-12-24 | Oreal | OXIDATION DYE COMPOSITION FOR KERATINIC FIBERS COMPRISING AN ASSOCIATIVE POLYMER AND A NACRANT AGENT |
FR2817467B1 (en) * | 2000-12-04 | 2003-01-10 | Oreal | DYE COMPOSITION FOR KERATINIC FIBERS COMPRISING AN ASSOCIATIVE POLYMER AND A POLYMER WITH ACRYLAMIDE PATTERNS, DIALKYLDIALLYLAMMONIUM HALIDE AND VINYL CARBOXYLIC ACID |
JP2002194073A (en) | 2000-12-26 | 2002-07-10 | Ge Plastics Japan Ltd | New polycarbonate-based resin and production method for the same |
FR2819404B1 (en) * | 2001-01-12 | 2004-11-05 | Oreal | COSMETIC COMPOSITIONS CONTAINING A FRUCTANE AND A CATIONIC POLYMER AND USES THEREOF |
FR2820031B1 (en) * | 2001-01-26 | 2006-05-05 | Oreal | COSMETIC COMPOSITION COMPRISING A FIXING POLYMER AND A CATIONIC POLY (VINYLLACTAM) |
FR2820312B1 (en) * | 2001-02-02 | 2003-05-02 | Oreal | PULVERULENT COMPOSITION FOR THE DECOLORATION OF HUMAN KERATINIC FIBERS |
FR2822683B1 (en) * | 2001-03-30 | 2005-01-28 | Oreal | COSMETIC COMPOSITIONS CONTAINING STARCH PHOSPHATE AND CATIONIC POLYMER AND USES THEREOF |
FR2822680B1 (en) * | 2001-03-30 | 2003-05-16 | Oreal | DETERGENT COSMETIC COMPOSITIONS CONTAINING AN ANIONIC SURFACTANT DERIVED FROM AMINO ACIDS AND A SOLUBLE CONDITIONING AGENT AND USES THEREOF |
FR2824734B1 (en) | 2001-05-16 | 2003-06-27 | Oreal | PULVERULENT COMPOSITION FOR THE DECOLORATION OF HUMAN KERATINIC FIBERS |
US6782456B2 (en) * | 2001-07-26 | 2004-08-24 | International Business Machines Corporation | Microprocessor system bus protocol providing a fully pipelined input/output DMA write mechanism |
FR2827761B1 (en) * | 2001-07-27 | 2005-09-02 | Oreal | COMPOSITION FOR THE OXIDATION STAIN OF KERATIN FIBERS COMPRISING A MONO- OR POLY-GLYCEROOLE FATTY ALCOHOL AND A PARTICULAR POLYOL |
FR2829385B1 (en) | 2001-09-11 | 2005-08-05 | Oreal | COSMETIC COMPOSITIONS CONTAINING METHACRYLIC ACID COPOLYMER, OIL AND USES THEREOF |
FR2829386B1 (en) * | 2001-09-11 | 2005-08-05 | Oreal | COSMETIC COMPOSITIONS CONTAINING A METHACRYLIC ACID COPOLYMER, A DIMETHICONE, A NACRANT AGENT AND A CATIONIC POLYMER AND USES THEREOF |
FR2829383B1 (en) * | 2001-09-11 | 2005-09-23 | Oreal | COSMETIC COMPOSITIONS CONTAINING A METHACRYLIC ACID COPOLYMER, A SILICONE AND A CATIONIC POLYMER AND USES THEREOF |
FR2829384B1 (en) * | 2001-09-11 | 2003-11-14 | Oreal | COSMETIC COMPOSITIONS CONTAINING A METHACRYLIC ACID COPOLYMER, A SILICONE AND A CATIONIC POLYMER AND USES THEREOF |
FR2830189B1 (en) | 2001-09-28 | 2004-10-01 | Oreal | LIGHTENING EFFECT DYE COMPOSITION FOR HUMAN KERATINIC FIBERS |
GB2381531A (en) * | 2001-11-02 | 2003-05-07 | Reckitt Benckiser Inc | Hard surface cleaning and disinfecting compositions |
FR2831814B1 (en) | 2001-11-08 | 2004-09-10 | Oreal | USES OF PARTICULAR AMINO SILICONES IN PRE- OR AFTER-TREATMENT OF KERATINIC FIBER DISCOLORATIONS |
FR2831803B1 (en) | 2001-11-08 | 2004-07-30 | Oreal | COSMETIC COMPOSITIONS CONTAINING AN AMINO SILICONE AND A THICKENING AGENT AND THEIR USES |
FR2831815B1 (en) | 2001-11-08 | 2004-08-06 | Oreal | REDUCING COMPOSITION FOR THE TREATMENT OF KERATINIC FIBERS COMPRISING A PARTICULAR AMINO SILICONE |
AU2002301803B2 (en) | 2001-11-08 | 2004-09-09 | L'oreal | Cosmetic compositions containing an aminosilicone and a conditioner, and uses thereof |
FR2831804B1 (en) | 2001-11-08 | 2004-07-30 | Oreal | PROCESS FOR PERMANENT DEFORMATION OF HAIR USING PARTICULAR AMINO SILICONES |
FR2831818B1 (en) | 2001-11-08 | 2004-07-16 | Oreal | OXIDIZING COMPOSITION FOR THE TREATMENT OF KERATINIC FIBERS COMPRISING A PARTICULAR AMINO SILICONE |
FR2831808B1 (en) * | 2001-11-08 | 2003-12-19 | Oreal | DYE COMPOSITION FOR KERATINIC FIBERS COMPRISING A PARTICULAR AMINO SILICONE |
FR2831807B1 (en) * | 2001-11-08 | 2004-10-01 | Oreal | DYE COMPOSITION FOR KERATINIC FIBERS COMPRISING A PARTICULAR AMINO SILICONE |
FR2832156B1 (en) * | 2001-11-15 | 2004-05-28 | Oreal | PREPARATION OF POLYSACCHARIDE BETAINATE COMPOUNDS, COMPOUNDS OBTAINED, THEIR USE AND COMPOSITIONS COMPRISING THE SAME |
FR2833837B1 (en) * | 2001-12-21 | 2005-08-05 | Oreal | COMPOSITION FOR KERATIN FIBER OXIDATION DYE COMPRISING COLZA OXYETHYLENE FATTY ACID AMIDE |
US7498022B2 (en) * | 2002-03-28 | 2009-03-03 | L'oreal S.A. | Cosmetic composition comprising at least one anionic surfactant, at least one cationic polymer and at least one amphiphilic, branched block acrylic copolymer and method for treating hair using such a composition |
US7232561B2 (en) * | 2002-05-31 | 2007-06-19 | L'oreal S.A. | Washing compositions comprising at least one amphiphilic block copolymer and at least one cationic or amphoteric polymer |
US7157413B2 (en) * | 2002-07-08 | 2007-01-02 | L'oreal | Detergent cosmetic compositions comprising an anionic surfactant, an amphoteric, cationic, and/or nonionic surfactant, and a polysacchardie, and use thereof |
FR2844712B1 (en) * | 2002-09-24 | 2006-06-02 | Oreal | COSMETIC COMPOSITION COMPRISING AN EXOGENOUS ADSORB OR FIXED-COVALENT LIGAND-RECEPTOR SYSTEM COMPRISING KERATINIC MATERIALS AND TREATING HAIRS USING THE SAME OR ITS CONSTITUENT ELEMENTS |
AU2003299070A1 (en) | 2002-09-26 | 2004-04-19 | L'oreal | Lipstick comprising a sequenced polymer |
MXPA03008714A (en) | 2002-09-26 | 2004-09-10 | Oreal | Sequenced polymers and cosmetic compositions comprising the same. |
US8007772B2 (en) | 2002-10-02 | 2011-08-30 | L'oreal S.A. | Compositions to be applied to the skin and the integuments |
US7147672B2 (en) * | 2002-10-21 | 2006-12-12 | L'oreal S.A. | Oxidation dyeing composition for keratin fibers comprising a cationic poly(vinyllactam) and at least one C10-C14 fatty acid, methods and devices for oxidation dyeing |
US7323015B2 (en) * | 2002-10-21 | 2008-01-29 | L'oreal S.A. | Oxidation dyeing composition for keratin fibers comprising a cationic poly(vinyllactam) and at least One C10-C14 fatty alcohol, methods and devices for oxidation dyeing |
JP2006518330A (en) | 2002-11-07 | 2006-08-10 | ロレアル | Cosmetic composition comprising at least one specific cyclic carbonate that may be polymerized |
US7326256B2 (en) * | 2002-12-06 | 2008-02-05 | L'ORéAL S.A. | Composition for the oxidation dyeing of keratin fibers, comprising at least one non-oxyalkenylated fatty alcohol, at least one oxidation dye, at least one associative polymer, and at least one amide of an alkanolamine and a C14-C30 fatty acid |
FR2848105B1 (en) | 2002-12-06 | 2006-11-17 | Oreal | OXIDATION DYEING COMPOSITION FOR KERATIN FIBERS COMPRISING FATTY ALCOHOL, OXIDATION DYE, ASSOCIATIVE POLYMER, AND C14-C30 ALKYL SULFATE |
US20040180030A1 (en) * | 2002-12-19 | 2004-09-16 | Mireille Maubru | Cosmetic compositions comprising at least one alkylamphohydroxyalkylsulphonate amphoteric surfactant and at least one nacreous agent and/or opacifier, and uses thereof |
GB0229806D0 (en) * | 2002-12-20 | 2003-01-29 | Unilever Plc | Fabric care composition |
US7261744B2 (en) | 2002-12-24 | 2007-08-28 | L'oreal S.A. | Method for dyeing or coloring human keratin materials with lightening effect using a composition comprising at least one fluorescent compound and at least one optical brightener |
US20040122807A1 (en) * | 2002-12-24 | 2004-06-24 | Hamilton Darin E. | Methods and systems for performing search interpretation |
US7226486B2 (en) * | 2003-01-16 | 2007-06-05 | L'oreal S.A | Ready-to-use bleaching compositions, preparation process and bleaching process |
US7217298B2 (en) * | 2003-01-16 | 2007-05-15 | L'oreal S.A. | Ready-to-use bleaching compositions, preparation process and bleaching process |
US7708981B2 (en) * | 2003-03-11 | 2010-05-04 | L'oreal S.A. | Cosmetic compositions comprising at least one crosslinked copolymer, at least one insoluble mineral particle and at least one polymer, and uses thereof |
US20050039270A1 (en) * | 2003-03-25 | 2005-02-24 | L'oreal S.A. | Use of polycarboxylic acids and salts thereof as complexing agents in oxidizing compositions for dyeing, bleaching or permanently reshaping keratin fibres |
US20050036970A1 (en) * | 2003-03-25 | 2005-02-17 | L'oreal S.A. | Reducing compositions for bleaching or permanently reshaping keratin fibres comprising polycarboxylic acids and salts thereof as complexing agents |
FR2852832B1 (en) * | 2003-03-25 | 2008-06-27 | Oreal | COLORING COMPOSITION FOR KERATIN FIBERS COMPRISING A HYDROXYCARBOXILIC ACID OR SALT, COMPOSITION READY FOR USE INCLUDING THE SAME, PROCESS FOR CARRYING OUT THE METHOD AND DEVICE |
US20050011017A1 (en) * | 2003-03-25 | 2005-01-20 | L'oreal S.A. | Oxidizing composition comprising hydroxycarboxylic acids and salts thereof as complexing agents for dyeing, bleaching or permanently reshaping keratin fibres |
US7303588B2 (en) * | 2003-03-25 | 2007-12-04 | L'oreal S.A. | Composition for dyeing keratinous fibers, comprising at least one polycarboxylic acid or a salt, ready-to-use composition comprising it, implementation process and device |
US7198650B2 (en) | 2003-04-01 | 2007-04-03 | L'oreal S.A. | Method of dyeing human keratin materials with a lightening effect with compositions comprising at least one fluorescent dye and at least one amphoteric or nonionic surfactant, composition thereof, process thereof, and device therefor |
US7195650B2 (en) | 2003-04-01 | 2007-03-27 | L'oreal S.A. | Process for dyeing, with a lightening effect, human keratin fibers that have been permanently reshaped, using at least one composition comprising at least one fluorescent dye |
US7208018B2 (en) | 2003-04-01 | 2007-04-24 | L'oreal | Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one associative polymer, process therefor and use thereof |
US7195651B2 (en) | 2003-04-01 | 2007-03-27 | L'oreal S.A. | Cosmetic composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one cationic polymer, and a dyeing process therefor |
US7186278B2 (en) | 2003-04-01 | 2007-03-06 | L'oreal S.A. | Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one compound comprising an acid functional group and processes therefor |
US7204860B2 (en) | 2003-04-01 | 2007-04-17 | L'oreal | Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one polyol, process therefor and use thereof |
US7192454B2 (en) | 2003-04-01 | 2007-03-20 | L'oreal S.A. | Composition for dyeing human keratin materials, comprising a fluorescent dye and a particular sequestering agent, process therefor and use thereof |
US7250064B2 (en) | 2003-04-01 | 2007-07-31 | L'oreal S.A. | Dye composition comprising at least one fluorescent dye and a non-associative thickening polymer for human keratin materials, process therefor, and method thereof |
US7147673B2 (en) | 2003-04-01 | 2006-12-12 | L'oreal S.A. | Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one insoluble polyorganosiloxane conditioning polymer, process therefor and use thereof |
US7303589B2 (en) | 2003-04-01 | 2007-12-04 | L'oreal S.A. | Process for dyeing human keratin fibers, having a lightening effect, comprising at least one fluorescent compound and compositions of the same |
US7736631B2 (en) | 2003-04-01 | 2010-06-15 | L'oreal S.A. | Cosmetic dye composition with a lightening effect for human keratin materials, comprising at least one fluorescent dye and at least one aminosilicone, and process of dyeing |
US7150764B2 (en) | 2003-04-01 | 2006-12-19 | L'oreal S.A. | Composition for dyeing a human keratin material, comprising at least one fluorescent dye and at least one insoluble conditioning agent, process thereof, use thereof, and devices thereof |
FR2854570B1 (en) * | 2003-05-09 | 2009-07-03 | Oreal | PROCESS FOR TREATING KERATIN FIBERS USING HEAT |
US20050063933A1 (en) * | 2003-06-17 | 2005-03-24 | Sabine Vrignaud | Cosmetic hair composition comprising isoeicosane and at least one nonsilicone fixing polymer |
US20050136027A1 (en) * | 2003-06-17 | 2005-06-23 | Sabine Vrignaud | Cosmetic hair composition based on isoeicosane and on a silicone fixing polyurethane |
US20050158265A1 (en) * | 2003-06-17 | 2005-07-21 | Sabine Vrignaud | Cosmetic hair composition comprising tridecyl trimellitate and at least one fixing polymer |
US7759296B2 (en) * | 2003-06-19 | 2010-07-20 | Lubrizol Advanced Materials, Inc. | Cationic polymers and fixative application therefor |
US7811552B2 (en) * | 2003-07-28 | 2010-10-12 | L'oreal S.A. | Cosmetic composition comprising a mixture of surfactants, a mixture of cationic polymers and a silicone |
US20050186151A1 (en) * | 2003-08-11 | 2005-08-25 | Franck Giroud | Cosmetic composition comprising stabilized and optionally coated metal particles |
US20050208005A1 (en) * | 2003-08-11 | 2005-09-22 | Franck Giroud | Cosmetic composition comprising particles having a core-shell structure |
FR2860143B1 (en) | 2003-09-26 | 2008-06-27 | Oreal | COSMETIC COMPOSITION COMPRISING A SEQUENCE POLYMER AND A NON-VOLATILE SILICONE OIL |
FR2861291A1 (en) * | 2003-10-24 | 2005-04-29 | Oreal | CAPILLARY COSMETIC COMPOSITION BASED ON FIXING POLYMERS AND COMPOUNDS LIKELY TO INFLATE UNDER THE ACTION OF HEAT. |
US8399001B2 (en) * | 2003-11-18 | 2013-03-19 | L'oreal | Cosmetic composition comprising at least one gellan gum or derivative thereof, at least one monovalent salt, and at least one suspension compound, processes using this composition, and uses thereof |
US20050186165A1 (en) * | 2003-11-18 | 2005-08-25 | Estelle Mathonneau | Cosmetic composition based on a cosmetically active compound and a gel comprising at least one crosslinked network of crosslinked polymer particles |
US8246940B2 (en) | 2003-11-18 | 2012-08-21 | L'oreal S.A. | Cosmetic composition comprising gellan gum or a derivative thereof, a fixing polymer, a monovalent salt and an alcohol, process of using the same |
US20050158262A1 (en) * | 2003-12-19 | 2005-07-21 | Eric Parris | Cosmetic composition comprising a cationic agent, a polymer comprising a hetero atom and an oil, and cosmetic treatment process |
FR2863884B1 (en) * | 2003-12-19 | 2007-06-29 | Oreal | CURING COMPOSITION COMPRISING, IN A MAJORITALLY AQUEOUS ENVIRONMENT, AN ELASTIC CATIONIC POLYURETHANE, METHODS USING SAME AND USES THEREOF |
FR2864776B1 (en) * | 2004-01-05 | 2006-06-23 | Oreal | COSMETIC COMPOSITION OF WATER-IN-WATER EMULSION TYPE BASED ON SURFACTANTS AND CATIONIC POLYMERS |
US20050175569A1 (en) * | 2004-01-07 | 2005-08-11 | Geraldine Fack | Cosmetic compositions comprising a cation, a drawing polymer and a thickener, and cosmetic treatment processes |
US20050232885A1 (en) * | 2004-01-07 | 2005-10-20 | L'oreal | Detergent cosmetic compositions comprising at least one surfactant, at least one drawing polymer and at least one nonsilicone conditioner, and use thereof |
US7294152B2 (en) * | 2004-01-07 | 2007-11-13 | L'oreal S.A. | Dyeing composition comprising at least one fluorindine compound for the dyeing of keratinic fibers, dyeing process comprising the composition and compound |
FR2867679B1 (en) * | 2004-03-17 | 2008-08-22 | Oreal | COSMETIC COMPOSITION COMPRISING MODIFIED POLYAMINES AND USES THEREOF. |
JP4082618B2 (en) * | 2004-03-22 | 2008-04-30 | ロレアル | Cosmetic composition containing a polyglycerolated silicone elastomer |
US8728451B2 (en) | 2004-03-25 | 2014-05-20 | L'oreal | Styling composition comprising, in a predominantly aqueous medium, a pseudo-block polymer, processes employing same and uses thereof |
US20050220723A1 (en) * | 2004-03-25 | 2005-10-06 | Katarina Benabdillah | Aerosol device comprising a propellant and a styling composition comprising, in a predominantly aqueous medium, a pseudo-block polymer and an additional fixing polymer; processes therefor and uses thereof |
FR2868305B1 (en) | 2004-04-02 | 2006-06-30 | Oreal | CAPILLARY TREATMENT PROCESS AND USE THEREOF |
US7976831B2 (en) * | 2004-04-02 | 2011-07-12 | L'oreal S.A. | Method for treating hair fibers |
US7981404B2 (en) | 2004-04-08 | 2011-07-19 | L'oreal S.A. | Composition for application to the skin, to the lips, to the nails, and/or to hair |
US20050257715A1 (en) * | 2004-04-08 | 2005-11-24 | Christophe Dumousseaux | Compositions for application to the skin, to the lips, to the nails, and/or to hair |
US20060025318A1 (en) * | 2004-04-22 | 2006-02-02 | Mireille Maubru | Composition for washing and conditioning keratin materials, comprising a carboxyalkyl starch, and process for the use thereof |
US20050287103A1 (en) * | 2004-06-08 | 2005-12-29 | Vanina Filippi | Cosmetic composition comprising at least one ester and at least one film-forming polymer |
FR2871376B1 (en) * | 2004-06-09 | 2007-06-22 | Oreal | COSMETIC COMPOSITION COMPRISING AS ANTI-TRANSPARENT AGENT A WATER-SOLUBLE POLYMER FLOCCULANT; PROCESS FOR TREATING TRANSPIRATION AND BODILY ODORS |
US20060013791A1 (en) * | 2004-07-16 | 2006-01-19 | L'oreal | Cosmetic composition comprising a defined silicone polymer and a film former |
FR2873035A1 (en) | 2004-07-16 | 2006-01-20 | Oreal | COSMETIC COMPOSITION COMPRISING A DEFINED SILICONE POLYMER AND A FILMOGENIC AGENT. |
US20060188461A1 (en) * | 2004-07-29 | 2006-08-24 | Cecile Bebot | Linear sulfonic polyester as a water-resistant hair fixing agent |
US20060024260A1 (en) * | 2004-07-29 | 2006-02-02 | Cecile Bebot | Cosmetic composition comprising a water-dispersible linear sulphonic polyester and a modified guar gum, methods employing this composition and uses |
FR2873576B1 (en) | 2004-07-29 | 2006-11-03 | Oreal | COSMETIC COMPOSITION COMPRISING A LINEAR SULFONIC POLYESTER AND A MODIFIED GUAR GUM, METHODS USING THE SAME AND USES THEREOF |
US20060024259A1 (en) * | 2004-07-29 | 2006-02-02 | Sabine Vrignaud | Cosmetic composition comprising, in a non-fatty medium, at least one linear sulfonic polyester and at least one nonionic thickening polymer, processes using this composition and uses thereof |
FR2873579B1 (en) | 2004-07-29 | 2006-11-03 | Oreal | COSMETIC COMPOSITION COMPRISING A LINEAR SULFONIC POLYESTER AND A PARTICULAR POLYURETHANE, METHODS USING THE SAME AND USES THEREOF |
US20060024261A1 (en) * | 2004-07-29 | 2006-02-02 | Bebot Cecile | Cosmetic compositions comprising a linear sulfonic polyester and a polyurethane, processes using these compositions and uses thereof |
US20060024255A1 (en) | 2004-07-30 | 2006-02-02 | L'oréal | Hair styling compositions comprising adhesive particles and non-adhesive particles |
FR2874820B1 (en) | 2004-09-08 | 2007-06-22 | Oreal | COSMETIC COMPOSITION BASED ON A CATIONIC SURFACTANT, A FATTY ALCOHOL AND A DIOL |
US20060057096A1 (en) * | 2004-09-08 | 2006-03-16 | Pascale Lazzeri | Cosmetic composition comprising at least one cationic surfactant, at least one aminated silicone, at least one fatty alcohol, and at least one diol |
US20060057094A1 (en) * | 2004-09-09 | 2006-03-16 | Estelle Mathonneau | Hair styling composition comprising at least one hydrophilic polymeric high porosity material and at least one fixing polymer |
FR2874824B1 (en) | 2004-09-09 | 2006-12-01 | Oreal | HAIR COMPOSITION COMPRISING THE ASSOCIATION OF HIGH-POROSITY HYDROPHILIC POLYMERIC MATERIAL AND FIXING POLYMER |
FR2875135B1 (en) | 2004-09-10 | 2006-12-01 | Oreal | COSMETIC COMPOSITION COMPRISING COMPOUNDS HAVING A CAGE STRUCTURE |
US20060062748A1 (en) * | 2004-09-10 | 2006-03-23 | Estelle Mathonneau | Cosmetic composition comprising at least one cage-like structure compound |
FR2876025B1 (en) | 2004-10-04 | 2007-02-09 | Oreal | HAIR COSMETIC COMPOSITION BASED ON HOLLOW PARTICLES AND SILICONE FIXING POLYURETHANE |
FR2876026B1 (en) | 2004-10-04 | 2007-02-09 | Oreal | HAIR-BASED COSMETIC COMPOSITION BASED ON HOLLOW PARTICLES AND NON-SILICONE FIXING POLYMER |
US9649261B2 (en) | 2004-10-05 | 2017-05-16 | L'oreal | Method of applying makeup to a surface and a kit for implementing such a method |
FR2876011B1 (en) | 2004-10-05 | 2006-12-29 | Oreal | METHOD FOR MAKE-UP A SUPPORT AND KIT FOR IMPLEMENTING SAID METHOD |
US20060088493A1 (en) * | 2004-10-13 | 2006-04-27 | Gabin Vic | Composition and process for the cosmetic treatment of keratin materials based on electrophilic monomers and non-silicone polymers |
US20060210507A1 (en) * | 2004-10-28 | 2006-09-21 | Ludivine Laurent | Cosmetic composition comprising at least one sulphonic polyester and at least one polyurethane |
FR2877215B1 (en) | 2004-10-28 | 2006-12-29 | Oreal | COSMETIC COMPOSITION COMPRISING A SULFONIC POLYESTER AND A POLYURETHANE |
FR2877927B1 (en) | 2004-11-16 | 2007-01-26 | Oreal | PRESSURIZED DEVICE FOR STAPPING CAPILAR FIBERS AND USE OF SUCH A DEVICE FOR SHAPING AND / OR MAINTAINING HAIR. |
US20060177399A1 (en) * | 2004-11-16 | 2006-08-10 | Herve Jourdan | Pressurized device for hair fiber styling and use of the same for hair fiber styling and/or hair |
FR2877926B1 (en) | 2004-11-16 | 2007-01-26 | Oreal | PRESSURIZED DEVICE FOR HAIRSTAPING CAPILLARY FIBERS AND USE OF SUCH A DEVICE FOR THE SHAPING AND / OR CARE OF CAPILLARY FIBERS. |
SI2319581T1 (en) * | 2004-11-26 | 2015-10-30 | Ucl Business Plc | Compositions comprising ornithine and phenylacetate or phenylbutyrate for treating hepatic encephalopathy |
US7429275B2 (en) * | 2004-12-23 | 2008-09-30 | L'oreal S.A. | Use of at least one compound chosen from porphyrin compounds and phthalocyanin compounds for dyeing human keratin materials, compositions comprising them, a dyeing process, and compounds therefor |
US20060171910A1 (en) * | 2004-12-30 | 2006-08-03 | Audrey Ricard | Cosmetic composition containing an alkoxylated alcohol ester and a hydrocarbon-based ester oil |
FR2881346B1 (en) | 2005-01-28 | 2007-04-27 | Oreal | CAPILLARY TREATMENT PROCESS AND USE THEREOF |
US7815901B2 (en) * | 2005-01-28 | 2010-10-19 | L'ORéAL S.A. | Hair treatment method |
DE102005010198A1 (en) * | 2005-03-05 | 2006-09-07 | Degussa Ag | Hydrolysis stable, post-crosslinked superabsorbent |
FR2883737B1 (en) | 2005-03-31 | 2009-06-12 | Oreal | COLORING COMPOSITION COMPRISING A GLYCERYLE ESTER AND A METHOD OF COLORING KERATIN FIBERS USING THE SAME |
US7442214B2 (en) * | 2005-03-31 | 2008-10-28 | L'oreal S.A. | Dye composition comprising at least one non-ionic associative polymer and process for dyeing keratin fibers using same |
FR2883746B1 (en) | 2005-03-31 | 2007-05-25 | Oreal | COLORING COMPOSITION COMPRISING A CELLULOSE AND METHOD FOR COLORING KERATIN FIBERS USING THE SAME |
US7550015B2 (en) | 2005-03-31 | 2009-06-23 | L'oreal S.A. | Dye composition with a reduced content of starting materials, and process for dyeing keratin fibers using the same |
US7578854B2 (en) | 2005-03-31 | 2009-08-25 | L'oreal S.A. | Dye composition comprising at least one fatty acid ester and process for dyeing keratin fibers using the same |
FR2883738B1 (en) | 2005-03-31 | 2007-05-18 | Oreal | COLORING COMPOSITION COMPRISING A NONIONIC ASSOCIATIVE POLYMER, METHOD FOR COLORING KERATIN FIBERS USING THE SAME |
FR2883736B1 (en) | 2005-03-31 | 2007-05-25 | Oreal | COLORING COMPOSITION COMPRISING A FATTY ACID ESTER AND METHOD FOR COLORING KERATIN FIBERS USING THE SAME |
FR2883735B1 (en) | 2005-03-31 | 2009-06-12 | Oreal | COLORING COMPOSITION WITH A REDUCED CONTENT OF RAW MATERIALS, METHOD FOR COLORING KERATINIC FIBERS USING THE SAME AND DEVICE |
US7575605B2 (en) | 2005-03-31 | 2009-08-18 | L'oreal S.A. | Dye composition comprising at least one glycerol ester and a process for dyeing keratin fibers using the composition |
FR2883734B1 (en) | 2005-03-31 | 2007-09-07 | Oreal | COLORING COMPOSITION WITH A REDUCED CONTENT OF RAW MATERIALS AND METHOD FOR COLORING KERATIN FIBERS USING THE SAME |
US7569078B2 (en) | 2005-03-31 | 2009-08-04 | L'oreal S.A. | Dye composition comprising at least one cellulose and process for dyeing keratin fibers using the dye composition |
US7651533B2 (en) | 2005-03-31 | 2010-01-26 | Oreal | Dye composition with a reduced content of starting materials, process for dyeing keratin fibers using the same and device therefor |
DE102005018924A1 (en) | 2005-04-22 | 2006-10-26 | Stockhausen Gmbh | Water-absorbing polymer structures with improved absorption properties |
DE102005018922A1 (en) * | 2005-04-22 | 2006-10-26 | Stockhausen Gmbh | Polycation-surface-treated water-absorbing polymer structure |
BRPI0610075B8 (en) | 2005-04-22 | 2021-06-22 | Evonik Degussa Gmbh | water absorbing polymer structures, their uses, processes for surface treatment thereof, compounds, processes for producing the same, products comprising the polymeric structures and uses of combinations of metal oxides and metal salts of divalent metal cation or trivalent |
DE102005021221A1 (en) | 2005-05-07 | 2006-11-09 | Geohumus International Gmbh & Co. Kg | Superabsorber with inorganic and organic ballast and additives |
US20060257339A1 (en) * | 2005-05-13 | 2006-11-16 | L'oreal | Use of conductive polymer nanofibers for treating keratinous surfaces |
US7666963B2 (en) * | 2005-07-21 | 2010-02-23 | Akzo Nobel N.V. | Hybrid copolymers |
US20070025944A1 (en) * | 2005-08-01 | 2007-02-01 | L'oreal | Cosmetic compositions useful for lengthening lashes |
FR2889921B1 (en) | 2005-08-30 | 2007-12-28 | Oreal | CONDITIONING AND APPLICATION ASSEMBLY COMPRISING A MAGNETIC DEVICE. |
US20070104747A1 (en) * | 2005-10-28 | 2007-05-10 | Virginie Masse | Cosmetic composition comprising at least one anti-dandruff agent and also oxyethylenated sorbitan monolaurate, and cosmetic treatment process using said composition |
US8586014B2 (en) * | 2005-10-28 | 2013-11-19 | L'oreal | Composition for the care of keratin material and cosmetic treatment process using said composition |
DE102005055497A1 (en) * | 2005-11-18 | 2007-05-31 | Stockhausen Gmbh | Odor-binding superabsorbent composition |
US20070190008A1 (en) * | 2005-12-20 | 2007-08-16 | Catherine Campain | Process for permanently reshaping the hair, comprising applying to the hair at least one precipitated fixing polymer, and multi-compartment device |
ITVA20050074A1 (en) * | 2005-12-23 | 2007-06-24 | Lamberti Spa | FILTER REDUCER FOR DRILLING SLUDGE |
US20070184002A1 (en) * | 2006-01-20 | 2007-08-09 | Sabine Vrignaud | Non-washing cosmetic composition comprising at least one ionic fixing polymer and at least one ester of polyethylene glycol and of fatty acid, and method for fixing a hairstyle |
US20070184001A1 (en) * | 2006-01-20 | 2007-08-09 | Sabine Vrignaud | Cosmetic composition comprising a nonionic fixing polymer and a specific ester of polyethylene glycol and of fatty acid, and a method for fixing the hairstyle |
CN101074300B (en) * | 2006-02-28 | 2012-10-03 | 赢创施托克豪森有限责任公司 | Good absorption and retention properties biodegradable superalborbent polymer composition |
DE102006019157A1 (en) * | 2006-04-21 | 2007-10-25 | Stockhausen Gmbh | Production of high-permeability, superabsorbent polymer structures |
BRPI0711452B8 (en) | 2006-04-21 | 2021-06-22 | Evonik Degussa Gmbh | process for preparing a water-absorbing polymeric structure, water-absorbing polymeric structure, composite, process for preparing a composite, use of the water-absorbent polymeric structure or use of the composite and use of a salt |
US20080019933A1 (en) * | 2006-07-21 | 2008-01-24 | L'oreal | Method of making-up dark skin |
NO20073834L (en) | 2006-07-21 | 2008-01-22 | Akzo Nobel Chemicals Int Bv | Sulfonated graft copolymers |
EP1897529A1 (en) * | 2006-07-21 | 2008-03-12 | L'oreal | Cosmetic composition |
FR2904320B1 (en) | 2006-07-27 | 2008-09-05 | Oreal | POLYMER SEQUENCES, AND PROCESS FOR THEIR PREPARATION |
FR2904536B1 (en) * | 2006-08-04 | 2008-11-07 | Oreal | COSMETIC COMPOSITION COMPRISING AT LEAST ONE CARRAGENAN LAMBDA-TYPE POLYSACCHARIDE AS AEROSOL, PROCESS FOR COSMETIC TREATMENT OF KERATIN FIBERS AND USE OF THE COMPOSITION |
FR2907678B1 (en) * | 2006-10-25 | 2012-10-26 | Oreal | KERATIN FIBER COLORING COMPOSITION COMPRISING POLYSILOXANE / POLYUREE BLOCK COPOLYMER |
DE102006060156A1 (en) * | 2006-12-18 | 2008-06-19 | Evonik Stockhausen Gmbh | Water-absorbing polymer structures produced using polymer dispersions |
FR2910274B1 (en) | 2006-12-22 | 2009-04-03 | Oreal | PROCESS FOR PERMANENT DEFORMATION OF KERATIN FIBERS COMPRISING AN APPLICATION STEP OF A LOW CONCENTRATED REDUCING COMPOSITION AND AN INTERMEDIATE DRYING STEP |
FR2911272B1 (en) | 2007-01-12 | 2009-03-06 | Oreal | REDUCING COMPOSITION INTENDED FOR USE IN A PROCESS FOR PERMANENTLY DEFORMING KERATIN FIBERS COMPRISING CYSTEINE AND THIOLACTIC ACID OR ONE OF THEIR SALTS |
DE102007007203A1 (en) | 2007-02-09 | 2008-08-14 | Evonik Stockhausen Gmbh | Water-absorbing polymer structure with high ammonia binding capacity |
FR2912936B1 (en) | 2007-02-23 | 2011-12-16 | Oreal | DEVICE FOR SPRAYING A BRILLIANCE COMPOSITION |
FR2912935B1 (en) | 2007-02-23 | 2009-05-15 | Oreal | DEVICE FOR SPRAYING A FIXATION COMPOSITION |
WO2008141093A1 (en) * | 2007-05-09 | 2008-11-20 | Buckman Laboratories International, Inc. | Asa sizing emulsions for paper and paperboard |
DE102007024080A1 (en) * | 2007-05-22 | 2008-11-27 | Evonik Stockhausen Gmbh | Process for gentle mixing and coating of superabsorbents |
FR2917972B1 (en) | 2007-06-29 | 2009-10-16 | Oreal | PASTE-FORMED ANHYDROUS COMPOSITION FOR KERATIN FIBER DECOLORATION |
DE102007030642A1 (en) | 2007-07-02 | 2009-01-08 | Momentive Performance Materials Gmbh | Process for the preparation of polyorganosiloxanes having (C6-C60) -alkylmethylsiloxy groups and dimethylsiloxy groups |
GB0712905D0 (en) | 2007-07-04 | 2007-08-15 | Reckitt Benckiser Uk Ltd | Hard surface treatment compositions with improved mold or fungi remediation properties |
US7816426B2 (en) * | 2007-07-16 | 2010-10-19 | Evonik Stockhausen, Llc | Superabsorbent polymer compositions having color stability |
FR2920977B1 (en) | 2007-09-14 | 2012-07-27 | Oreal | COSMETIC COMPOSITIONS CONTAINING A CATIONIC COPOLYMER AND A PARTICULAR TRIGLYCERIDE AND USES THEREOF. |
FR2920978B1 (en) | 2007-09-14 | 2012-04-27 | Oreal | COSMETIC COMPOSITION COMPRISING CATIONIC COPOLYMER AND STARCH AND METHOD OF COSMETIC TREATMENT. |
FR2920972B1 (en) | 2007-09-14 | 2009-12-04 | Oreal | COSMETIC COMPOSITION COMPRISING A PARTICULAR CATIONIC POLYMER AND AT LEAST ONE C8-C24 FATTY ACID ESTER AND SORBITAN OXYETHYLENE COMPRISING 2 TO 10 OXYETHYLENE MOTIFS, AND COSMETIC TREATMENT METHOD. |
FR2920976B1 (en) | 2007-09-14 | 2009-12-04 | Oreal | COSMETIC COMPOSITION COMPRISING A CATIONIC COPOLYMER AND ANIONIC ASSOCIATIVE POLYMER AND COSMETIC PROCESSING METHOD. |
FR2920971B1 (en) | 2007-09-14 | 2014-03-28 | Oreal | COSMETIC COMPOSITION COMPRISING AT LEAST ONE PARTICULAR CATIONIC POLYMER, AT LEAST ONE SURFACE ACTIVE AGENT, AT LEAST ONE CATIONIC OR AMPHOTERIC POLYMER AND AT LEAST ONE MINERAL PARTICLE, AND METHOD OF COSMETIC TREATMENT. |
DE102007045724B4 (en) | 2007-09-24 | 2012-01-26 | Evonik Stockhausen Gmbh | Superabsorbent composition with tannins for odor control, process for their preparation and use |
DE102007053619A1 (en) | 2007-11-08 | 2009-05-20 | Evonik Stockhausen Gmbh | Water-absorbing polymer structures with improved color stability |
FR2924336A1 (en) | 2007-11-30 | 2009-06-05 | Oreal | HAIR COMPOSITION COMPRISING (METH) ACRYLIC COPOLYMERS AND AT LEAST ONE OIL. |
FR2924338B1 (en) | 2007-11-30 | 2010-09-03 | Oreal | HAIR COMPOSITION COMPRISING AT LEAST ONE (METH) ACRYLIC COPOLYMER AND AT LEAST ONE NACRANT AGENT. |
FR2924337A1 (en) | 2007-11-30 | 2009-06-05 | Oreal | REPOSITIONABLE HAIR COMPOSITION COMPRISING AT LEAST ONE (METH) ACRYLIC COPOLYMER AND AT LEAST ONE SILICONE. |
TWI455973B (en) * | 2008-03-05 | 2014-10-11 | Evonik Degussa Gmbh | Superabsorbent composition with zinc salicylate for odour control |
JP5582517B2 (en) | 2008-03-13 | 2014-09-03 | ハイモ株式会社 | Hair cosmetic additive and hair cosmetic containing the same |
FR2930441B1 (en) | 2008-04-28 | 2010-05-28 | Oreal | COSMETIC COMPRESSION COMPRISING A CATIONIC POLYRETHANE AND A CELLULOSE DERIVATIVE AND STAPLING USES |
FR2930440B1 (en) | 2008-04-28 | 2012-12-14 | Oreal | COSMETIC COMPOSITION COMPRISING A CATIONIC POLYURETHANE AND A PARTICULAR POLYACRYLATE AND USES THEREFOR |
FR2930436B1 (en) | 2008-04-28 | 2010-06-11 | Oreal | COSMETIC COMPOSITION COMPRISING AN EMULSION OBTAINED BY A PIT METHOD |
FR2930442B1 (en) | 2008-04-28 | 2010-06-11 | Oreal | COSMETIC COMPOSITION COMPRISING EMULSION OBTAINED BY PIT METHOD |
FR2939657B1 (en) | 2008-12-15 | 2011-02-11 | Oreal | COSMETIC COMPOSITION COMPRISING A POLYAMINE CARRYING DIAZIRIN GROUPS AND USE FOR THE PHOTO-GRAFTING OF A NON-SACCHARIDE POLYMER DIFFERENT FROM POLYAMINE POLYMERS |
WO2010076484A1 (en) | 2008-12-16 | 2010-07-08 | L'oreal | Anhydrous cosmetic composition containing a polyester, a volatile oil, and a non-volatile oil |
WO2010076483A1 (en) | 2008-12-16 | 2010-07-08 | L'oreal | Cosmetic composition containing a polyester, an organic oil and water |
FR2940078B1 (en) | 2008-12-19 | 2011-05-13 | Oreal | COMPOSITION COMPRISING A FATTY BODY AND A CATIONIC POLYMER, A METHOD FOR COLORING THE SAME AND DEVICES |
FR2940067B1 (en) | 2008-12-19 | 2011-02-25 | Oreal | OXIDIZING COMPOSITION FOR THE TREATMENT OF KERATIN FIBERS COMPRISING A CATIONIC POLYMER, A FATTY AMIDE AND AN OXYGEN AGENT |
FR2940063B1 (en) | 2008-12-19 | 2011-02-11 | Oreal | ANTI-TRANSPIRANT COMPOSITIONS CONTAINING AT LEAST ONE COMPOUND FORMED BY THE ASSOCIATION OF AT LEAST ONE ANIONIC SPECIES AND AT LEAST ONE CATIONIC SPECIES AND METHOD OF TREATING HUMAN PERSPIRATION |
EP2198850A1 (en) | 2008-12-22 | 2010-06-23 | L'oreal | Cosmetic composition containing four types of surfactants and one non-silicone fatty derivative |
FR2940094B1 (en) | 2008-12-22 | 2011-02-25 | Oreal | DETERGENT COSMETIC COMPOSITION COMPRISING FOUR SURFACTANTS, CATIONIC POLYMER AND ZINC SALT |
US8557226B2 (en) | 2009-01-16 | 2013-10-15 | Isp Investments Inc. | Performance-boosting UV-absorbing compounds |
US9044623B2 (en) | 2009-01-27 | 2015-06-02 | Isp Investments Inc. | Polymer-bound UV absorbers in personal care compositions |
FR2941621B1 (en) | 2009-01-30 | 2011-04-01 | Oreal | COSMETIC COMPOSITION COMPRISING A PARTICULAR ALKOXYSILANE AND A MICROBIAL GUM AND USES THEREFOR |
DE102009016404A1 (en) | 2009-04-07 | 2010-10-21 | Evonik Stockhausen Gmbh | Use of hollow bodies for producing water-absorbing polymer structures |
FR2944438B1 (en) | 2009-04-15 | 2011-06-17 | Oreal | METHOD OF FORMING HAIR BY MEANS OF REDUCING COMPOSITION AND HEATING. |
WO2010133658A2 (en) | 2009-05-22 | 2010-11-25 | L'oréal | A cosmetic composition comprising at least one elastomeric anionic polyurethane and at least one non-ionic thickener |
WO2010133660A2 (en) | 2009-05-22 | 2010-11-25 | L'oreal | Cosmetic composition comprising at least one elastomeric polyurethane |
US20100297051A1 (en) * | 2009-05-22 | 2010-11-25 | Feuillette Laetitia | Cosmetic composition comprising at least one elastomeric anionic polyurethane and at least one non-ionic thickener |
US20100297052A1 (en) * | 2009-05-22 | 2010-11-25 | Feuillette Laetitia | Cosmetic composition comprising at least one elastomeric polyurethane |
US8673272B2 (en) * | 2009-07-27 | 2014-03-18 | Isp Investments Inc. | Ultraviolet-absorbing compounds |
CN102574961B (en) | 2009-07-31 | 2015-09-23 | 阿克佐诺贝尔股份有限公司 | Hybrid copolymer composition |
DE102009040949A1 (en) | 2009-09-11 | 2011-03-31 | Evonik Stockhausen Gmbh | Plasma modification of water-absorbing polymer structures |
FR2949970B1 (en) | 2009-09-15 | 2011-09-02 | Oreal | USE OF A SICCATIVE OIL FOR PROTECTING THE COLOR FROM THE WASHING OF KERATINIC FIBERS ARTIFICIALLY DYED; COLORING PROCESSES |
FR2954149B1 (en) | 2009-12-17 | 2014-10-24 | Oreal | COSMETIC COMPOSITION COMPRISING A SURFACTANT, A LIQUID FATTY ALCOHOL AND A NONIONIC ASSOCIATIVE POLYMER AND COSMETIC TREATMENT METHOD |
FR2954114B1 (en) | 2009-12-17 | 2013-10-11 | Oreal | COSMETIC COMPOSITION COMPRISING SURFACTANT, LIQUID GRADE ALCOHOL AND OXYETHYLENE FATTY ALCOHOL ETHER AND COSMETIC TREATMENT METHOD |
ES2660699T3 (en) | 2009-12-18 | 2018-03-23 | L'oréal | Procedure for the treatment of keratin fibers |
FR2954112B1 (en) | 2009-12-23 | 2013-02-22 | Oreal | COSMETIC COMPOSITION COMPRISING AT LEAST ONE VOLATILE LINEAR ALKANE, AT LEAST ONE CATIONIC SURFACTANT IN A CATIONIC (S) VOLATILE (S) / CATIONIC SURFACTANT (S) SPECIFIC CATIONIC SURFACE RATIO (S) |
FR2954129B1 (en) * | 2009-12-23 | 2012-03-02 | Oreal | COSMETIC COMPOSITION COMPRISING AT LEAST ONE ORGANIC COMPOUND OF THE SILICON, AT LEAST TWO ANIONIC SURFACTANTS AND AT LEAST ONE AMPHOTERIC SURFACTANT |
FR2954154B1 (en) | 2009-12-23 | 2012-02-24 | Oreal | COSMETIC COMPOSITION COMPRISING AT LEAST ONE VOLATILE LINEAR ALKANE, AT LEAST ONE SILICONE AND AT LEAST ONE FAT BODY IN A PARTICULAR BODY / SILICONE RATIO |
FR2954135B1 (en) | 2009-12-23 | 2012-02-24 | Oreal | COSMETIC COMPOSITION COMPRISING AT LEAST ONE ORGANIC COMPOUND OF THE SILICON, AT LEAST ONE ANIONIC SURFACTANT AND AT LEAST ONE AMINO SILICONE, AND A PROCESS USING THE SAME |
FR2954108B1 (en) | 2009-12-23 | 2012-03-09 | Oreal | USE OF A COSMETIC COMPOSITION COMPRISING A VOLATILE LINEAR ALKANE AND A NONIONIC ASSOCIATIVE POLYMER FOR CONDITIONING HAIR |
FR2954128B1 (en) * | 2009-12-23 | 2012-02-17 | Oreal | COSMETIC COMPOSITION COMPRISING AT LEAST ONE ORGANIC COMPOUND OF THE SILICON, AT LEAST ONE ANIONIC SURFACTANT AND AT LEAST ONE NONIONIC THICKENING AGENT AS WELL AS A PROCESS IMPLEMENTING THE COMPOSITION |
FR2954139B1 (en) | 2009-12-23 | 2012-05-11 | Oreal | COSMETIC COMPOSITION COMPRISING AT LEAST ONE VOLATILE LINEAR ALKANE AND AT LEAST ONE NON-PROTEIN CATIONIC POLYMER |
FR2954107B1 (en) | 2009-12-23 | 2012-04-20 | Oreal | COSMETIC COMPOSITION IN THE FORM OF NANOEMULSION CONTAINING VOLATILE LINEAR ALKANE |
FR2954100B1 (en) | 2009-12-23 | 2012-03-09 | Oreal | COSMETIC COMPOSITION COMPRISING AT LEAST ONE ORGANIC COMPOUND OF THE SILICON, AT LEAST ONE ANIONIC SURFACTANT AND AT LEAST ONE CATIONIC POLYMER |
FR2956809B1 (en) | 2010-03-01 | 2014-09-26 | Oreal | COMPOSITION COMPRISING ELLAGIC ACID AND A PARTICULAR CATIONIC SURFACTANT AND USE THEREOF IN COSMETICS |
DE102010004478A1 (en) | 2010-01-12 | 2011-07-14 | Riesinger, Birgit, 48346 | New technologies for use in wound dressings with superabsorbent polymers |
FR2956808B1 (en) | 2010-03-01 | 2012-05-25 | Oreal | USE OF ELLAGIC ACID AS ANTI-FILM AGENT. |
WO2011107467A2 (en) | 2010-03-01 | 2011-09-09 | L'oreal | Cosmetic composition based on ellagic acid or a derivative thereof and on a particular mixture of surfactants |
FR2956812B1 (en) | 2010-03-01 | 2013-03-08 | Oreal | COSMETIC COMPOSITION BASED ON ELLAGIC ACID OR ONE OF ITS DERIVATIVES AND A BACTERIA EXTRACT. |
FR2956811B1 (en) | 2010-03-01 | 2012-05-25 | Oreal | COSMETIC ANTI-FILM COMPOSITION BASED ON ELLAGIC ACID OR ONE OF ITS DERIVATIVES AND A SECOND ACTIVE DIFFERENT COMPOUND IN A PARTICULAR PONDERAL RATIO. |
EP2371869A1 (en) | 2010-03-30 | 2011-10-05 | Evonik Stockhausen GmbH | A process for the production of a superabsorbent polymer |
PL224855B1 (en) * | 2010-04-22 | 2017-02-28 | Univ Jagielloński | The use of modified polysaccharides for heparin neutralization |
FR2959666B1 (en) | 2010-05-07 | 2012-07-20 | Oreal | FOAMING COSMETIC COMPOSITION BASED ON ELLAGIC ACID OR ONE OF ITS DERIVATIVES AND ESSENTIAL OIL. |
FR2961395B1 (en) | 2010-06-17 | 2012-07-27 | Oreal | COSMETIC COMPOSITION COMPRISING A BRANCHED SULFONIC POLYESTER AND A PARTICULATE THICKENER AND STAPLING USES |
FR2964317B1 (en) | 2010-09-06 | 2013-04-12 | Oreal | COSMETIC COMPOSITION COMPRISING A FIXING POLYMER AND A PARTICULAR THICKENER AND STAPLING USES |
FR2964319B1 (en) | 2010-09-06 | 2017-01-13 | Oreal | COSMETIC COMPOSITION COMPRISING AT LEAST ONE CATIONIC POLYMER AND AT LEAST TWO SURFACTANTS |
WO2012032673A1 (en) | 2010-09-08 | 2012-03-15 | L'oreal | Cosmetic composition for keratin fibers |
FR2964565B1 (en) | 2010-09-14 | 2012-09-07 | Oreal | COSMETIC COMPOSITION COMPRISING A FIXING POLYMER AND ANTIPELLICULAR AGENT |
FR2965174B1 (en) | 2010-09-24 | 2013-04-12 | Oreal | COSMETIC COMPOSITION COMPRISING AT LEAST ONE HYGROSCOPIC SALT, AT LEAST ONE AROMATIC POLYOL ETHER AND AT LEAST ONE DIOL, COSMETIC PROCESSING PROCESS |
FR2965481B1 (en) | 2010-10-01 | 2013-04-19 | Oreal | PROCESS FOR TREATING KERATIN FIBERS USING AT LEAST ONE SULFUR REDUCER, AT LEAST ONE CATIONIC POLYMER AND AT LEAST ONE MERCAPTOSILOXANE |
WO2012049145A1 (en) | 2010-10-12 | 2012-04-19 | L'oreal | Cosmetic composition comprising a particular silicon derivative and one or more acrylic thickening polymers |
FR2966357A1 (en) | 2010-10-26 | 2012-04-27 | Oreal | COSMETIC COMPOSITION COMPRISING A FATTY CHAIN ALCOXYSILANE AND ANTIPELLICULAR AGENT |
FR2966352B1 (en) | 2010-10-26 | 2016-03-25 | Oreal | COSMETIC COMPOSITION COMPRISING A FATTY CHAIN ALCOXYSILANE AND A CATIONIC POLYMER |
FR2966725B1 (en) | 2010-11-02 | 2013-02-22 | Oreal | COLORING COMPOSITION WITH LOW AMMONIA CONTENT |
US20120128616A1 (en) | 2010-11-19 | 2012-05-24 | Voisin Sebastien | Cosmetic composition comprising at least one elastomeric polyurethane and at least one cationic polymer |
FR2968209B1 (en) | 2010-12-03 | 2013-07-12 | Oreal | COSMETIC COMPOSITIONS CONTAINING NON-AMINOUS SILICONE, LIQUID FATTY ESTER AND AMINO SILICONE, METHODS AND USES |
FR2968943B1 (en) | 2010-12-21 | 2013-07-05 | Oreal | COSMETIC COMPOSITION COMPRISING A ZINC SALT, A CATIONIC POLYMER AND A PROPELLING AGENT |
WO2012091502A2 (en) | 2010-12-30 | 2012-07-05 | 주식회사 케이씨아이 | Polysaccharide-based graft copolymer and composition comprising same for personal care |
FR2971157B1 (en) | 2011-02-08 | 2013-10-04 | Oreal | METHOD FOR APPLYING A CAPILLARY COMPOSITION TO HAIR |
FR2971938B1 (en) | 2011-02-25 | 2013-08-02 | Oreal | COMPOSITION FOR COLORING KERATINIC FIBERS COMPRISING DIRECT COLOR WITH DISULFURE / THIOL FUNCTION, LOW OR NON-ETHOXYL FATTY ALCOHOL, CATIONIC SURFACTANT, ALKALINE AGENT, AND REDUCING AGENT |
FR2971939B1 (en) | 2011-02-25 | 2013-02-15 | Oreal | COMPOSITION FOR COLORING KERATINIC FIBERS COMPRISING A DIRECT DYE WITH DISULFIDE / THIOL FUNCTION, A FATTY BODY, AN ALKALI AGENT, AND A REDUCING AGENT |
FR2971935B1 (en) | 2011-02-25 | 2013-02-15 | Oreal | COMPOSITION FOR COLORING KERATIN FIBERS COMPRISING DIRECT COLOR WITH DISULFIDE / THIOL FUNCTION, THICKENING POLYMER, NON-IONIC SURFACTANT, ALKALINE AGENT, AND REDUCING AGENT |
FR2971936B1 (en) | 2011-02-25 | 2013-02-15 | Oreal | COMPOSITION FOR COLORING KERATIN FIBERS COMPRISING DIRECT DYE WITH DISULFIDE / THIOL FUNCTION, NON-IONIC SURFACTANT, AMPHOTERIC SURFACTANT, ETHOXYL FATTY ALCOHOL, ALKALINE AGENT, AND REDUCING AGENT |
FR2971937B1 (en) | 2011-02-25 | 2013-02-15 | Oreal | COMPOSITION FOR COLORING KERATIN FIBERS COMPRISING A DIRECT DYE WITH DISULFURE / THIOL FUNCTION, A NON-CELLULOSIC THICKENING POLYMER, AN ALKALI AGENT, AND A REDUCING AGENT |
EP2677996B1 (en) | 2011-02-25 | 2017-11-29 | L'Oréal | Composition for dyeing keratinous fibres comprising a direct dye having a disulphide/thiol functional group, a thickening polymer, an ethoxylated fatty alcohol and/or a nonionic surfactant, an alkaline agent and a reducing agent |
FR2973661A1 (en) | 2011-04-08 | 2012-10-12 | Oreal | METHOD FOR TREATING HAIR |
WO2012149617A1 (en) | 2011-05-04 | 2012-11-08 | L'oreal S.A. | Detergent cosmetic compositions comprising four surfactants, a cationic polymer and a silicone, and use thereof |
FR2975593B1 (en) | 2011-05-27 | 2013-05-10 | Oreal | COMPOSITION COMPRISING ALCOXYSILANE AND MODIFIED STARCH AND USE THEREOF IN COSMETICS |
FR2975594B1 (en) | 2011-05-27 | 2013-05-10 | Oreal | COMPOSITION COMPRISING ALCOXYSILANE, FATTY ESTER AND SILICONE AND USE THEREOF IN COSMETICS |
FR2976483B1 (en) | 2011-06-17 | 2013-07-26 | Oreal | COSMETIC COMPOSITION COMPRISING ANIONIC SURFACTANT, NONIONIC OR AMPHOTERIAL SURFACTANT AND SOLID FATTY ALCOHOL, AND COSMETIC TREATMENT METHOD |
FR2977482B1 (en) | 2011-07-05 | 2013-11-08 | Oreal | COLORING COMPOSITION USING A LONG CHAIN ETHER OF ALCOXYL FATTY ALCOHOL AND CATIONIC POLYMER, METHODS AND DEVICES |
RU2666399C2 (en) | 2011-07-05 | 2018-09-07 | Л'Ореаль | Dye composition comprising an alkoxylated fatty alcohol ether and a fatty alcohol |
EP2729120B1 (en) | 2011-07-05 | 2019-08-21 | L'oreal | Cosmetic composition rich in fatty substances comprising a polyoxyalkylenated fatty alcohol ether and a direct dye and/or an oxidation dye, the dyeing method and the device |
WO2013042274A1 (en) | 2011-09-22 | 2013-03-28 | L'oreal | Cosmetic cleansing composition |
BR112014008874A2 (en) | 2011-11-04 | 2017-04-25 | Akzo Nobel Chemicals Int Bv | dendrite hybrid copolymer composition |
WO2013064648A1 (en) | 2011-11-04 | 2013-05-10 | Akzo Nobel Chemicals International B.V. | Graft dendrite copolymers, and methods for producing the same |
DE102011086522A1 (en) | 2011-11-17 | 2013-05-23 | Evonik Degussa Gmbh | Superabsorbent polymers for highly filled or fiber-free hygiene articles |
FR2984136B1 (en) | 2011-12-19 | 2013-12-20 | Oreal | COSMETIC COMPOSITION COMPRISING AN ANIONIC OR NON-IONIC ASSOCIATIVE POLYMER, A FIXING POLYMER AND A PARTICULAR SURFACTANT AND USE IN STAPLING |
FR2984135B1 (en) | 2011-12-19 | 2013-12-20 | Oreal | COSMETIC COMPOSITION COMPRISING AN ANIONIC OR NON-IONIC ASSOCIATIVE POLYMER, A FIXING POLYMER AND A PARTICULAR SURFACTANT AND USE IN STAPLING |
FR2984159B1 (en) | 2011-12-19 | 2014-01-31 | Oreal | COSMETIC COMPOSITION COMPRISING HYDROPHOBICALLY MODIFIED CELLULOSE, ANIONIC SULFATE OR SULFONATE SURFACTANT, AND BRANCHED ALCOHOL. |
FR2984156B1 (en) | 2011-12-19 | 2016-08-26 | Oreal | COSMETIC COMPOSITION COMPRISING A HYDROPHOBICALLY MODIFIED CELLULOSE AND AN ANIONIC SURFACTANT WITH A (S) CARBOXYLATE (S) GROUP |
WO2013093332A2 (en) | 2011-12-20 | 2013-06-27 | L'oreal | Cosmetic composition comprising an anionic surfactant, a solid fatty alcohol and a solid fatty ester, and cosmetic treatment process |
FR2985905B1 (en) | 2012-01-23 | 2014-10-17 | Oreal | COMPOSITION COMPRISING AT LEAST ONE PARTICULAR ALCOXYSILANE POLYMER |
EP2825583B1 (en) | 2012-03-15 | 2016-09-14 | Huntsman P&A Uerdingen GmbH | Method for granulating particle-containing material obtained from industrial processes, the granulate thus produced |
DE102012102473A1 (en) | 2012-03-22 | 2013-09-26 | Xtract Gmbh | Treating sewage sludge, useful for improving its storage- and/or transport properties, comprises mechanically dewatering sludge, and mixing dewatered sludge with superabsorbent or hydrogel to obtain granules with specific moisture content |
FR2988602B1 (en) | 2012-03-27 | 2014-09-05 | Oreal | COSMETIC PROCESS OF CARE AND / OR MAKE-UP OF KERATINIC MATERIALS |
EP3769817A1 (en) | 2012-03-30 | 2021-01-27 | L'oreal Sa | Composition comprising (2,5-diaminophenyl) ethanol and a carboxylic anionic polymer in a medium rich in fatty substances, dyeing process and device |
FR2989880B1 (en) | 2012-04-26 | 2016-07-01 | Oreal | PRESSURIZED COSMETIC COMPOSITION COMPRISING A FATTY CHAIN SILANE |
FR2990131B1 (en) | 2012-05-07 | 2015-12-25 | Oreal | AEROSOL DEVICE BASED ON CALCIUM SALT AND FIXING POLYMER |
ES2690780T3 (en) | 2012-06-07 | 2018-11-22 | L'oreal | Hair molding process using fatty bodies |
FR2991875B1 (en) | 2012-06-15 | 2015-10-02 | Oreal | COMPOSITION COMPRISING A DYARBOXYLIC PYRIDINE ACID ESTER AND A FIXING POLYMER, METHOD AND USE |
FR2992199B1 (en) | 2012-06-21 | 2015-07-17 | Oreal | COSMETIC COMPOSITION COMPRISING AQUEOUS DISPERSION OF HYDROPHOBIC SILICA AEROGEL PARTICLES AND A PARTICULAR ALCOHOL |
WO2013190080A2 (en) | 2012-06-21 | 2013-12-27 | L'oreal | Cosmetic composition comprising hydrophobic silica aerogel particles, a wax, a hydrocarbon oil and a fatty alcohol and/or a fatty acid |
FR2992177B1 (en) | 2012-06-21 | 2014-06-20 | Oreal | COSMETIC COMPOSITION COMPRISING SILICA HYDROPHOBIC AEROGEL PARTICLES AND A FIXING POLYMER |
JP6257535B2 (en) | 2012-06-29 | 2018-01-10 | ロレアル | Cosmetic composition for keratin fibers |
FR2994084B1 (en) | 2012-08-02 | 2014-10-31 | Oreal | CREAM-STAINING COMPOSITION COMPRISING AT LEAST ONE OIL, NO LITTLE OR LESS SOLID FATTY ALCOHOL, COLORING PROCESS AND APPROPRIATE DEVICE |
ES2709026T5 (en) | 2012-08-02 | 2022-12-22 | Oreal | Dyeing composition comprising at least one fatty substance, at least one oxidizing agent and at least one nonionic, anionic and amphoteric surfactant |
RU2015106932A (en) | 2012-08-02 | 2016-09-20 | Л'Ореаль | COMPOSITION FOR DYEING, CONTAINING A FATTY SUBSTANCE, NON-ION GUAR GUM, AMPHOTERIC SURFACE-ACTIVE SUBSTANCE AND NON-IONIC OR ANION SURFACE SUBSTANCE ORANGE |
FR2994091B1 (en) | 2012-08-02 | 2014-08-01 | Oreal | COLORING COMPOSITION COMPRISING NON-IONIC GUAR GUM OR ONE OF ITS NON-IONIC DERIVATIVES, PROCESS AND DEVICE |
FR2994388B1 (en) | 2012-08-07 | 2014-09-05 | Oreal | COSMETIC COMPOSITION COMPRISING AT LEAST ONE PARTICULAR FIXING POLYMER AND AT LEAST ONE PARTICULAR THICKENING POLYMER |
FR2994385B1 (en) | 2012-08-07 | 2016-10-28 | Oreal | BIPHASIC COSMETIC COMPOSITION CONDITIONED IN BOTTLE-PUMP |
WO2014056962A2 (en) | 2012-10-11 | 2014-04-17 | L'oreal | Cosmetic composition comprising a bacterial lysate, a thickener and a particular surfactant system, and cosmetic treatment process |
WO2014068795A1 (en) | 2012-10-31 | 2014-05-08 | L'oreal | Use of triazine derivatives for permanent deformation of keratin fibers |
DE102012220400A1 (en) | 2012-11-09 | 2014-05-15 | Evonik Industries Ag | Superabsorber for cable applications |
FR2997848B1 (en) | 2012-11-09 | 2015-01-16 | Oreal | COMPOSITION COMPRISING A DICARBONYL DERIVATIVE AND A METHOD FOR SMOOTHING THE HAIR THEREFROM |
FR2997844B1 (en) | 2012-11-09 | 2014-12-05 | Oreal | COMPOSITION COMPRISING A DICARBONYL COMPOUND AND A METHOD FOR SMOOTHING THE HAIR THEREFROM |
FR2997845B1 (en) | 2012-11-09 | 2015-03-06 | Oreal | METHOD FOR SMOOTHING A HAIR FROM A COMPOSITION CONTAINING GLYOXYLIC ACID AND / OR ONE OF ITS DERIVATIVES |
FR2999078B1 (en) | 2012-12-11 | 2015-08-07 | Oreal | COSMETIC COMPOSITION COMPRISING THE NONIONIC AND CATIONIC SURFACTANT ASSOCIATION AND METHOD OF COSMETIC TREATMENT |
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FR2999423B1 (en) | 2012-12-14 | 2015-03-13 | Oreal | COSMETIC POWDER COMPOSITION COMPRISING A (METH) ACRYLIC THICKENING POLYMER, A FIXING POLYMER, WATER-INSOLUBLE PARTICLES |
FR3001144B1 (en) | 2013-01-18 | 2015-07-17 | Oreal | FLEXIBLE SOLID COSMETIC COMPOSITION COMPRISING ANIONIC SURFACTANTS AND POLYMERIC CONDITIONING AGENTS, AND COSMETIC TREATMENT METHOD |
FR3001147B1 (en) | 2013-01-18 | 2015-07-17 | Oreal | FLEXIBLE SOLID COSMETIC COMPOSITION COMPRISING ANTI-ANSIAL SURFACTANTS AND SOLID PARTICLES, AND COSMETIC TREATMENT METHOD |
FR3001145B1 (en) | 2013-01-18 | 2015-07-17 | Oreal | FLEXIBLE SOLID COSMETIC COMPOSITION COMPRISING ANIO-NITIC SURFACTANTS AND POLYOLS, AND COSMETIC TREATMENT METHOD |
FR3001149B1 (en) | 2013-01-18 | 2015-01-16 | Oreal | METHOD OF FORMING HAIR IN WHICH A PARTICULAR HAIRING COMPOSITION IS APPLIED THAT WE ONLY RINSE |
FR3002143B1 (en) | 2013-02-15 | 2015-02-20 | Oreal | COSMETIC COMPOSITION COMPRISING A VINYLFORMAMIDE / VINYLFORMAMINE COPOLYMER, A CELLULOSIC THICKENING POLYMER AND AN AMPHOTERE OR ZWITTERIONIC SURFACTANT |
FR3004902A1 (en) | 2013-04-30 | 2014-10-31 | Oreal | MULTI-ORIFICE DIFFUSION AEROSOL DEVICE FOR SHAPING HAIR AND / OR MAINTAINING HAIR |
FR3004929B1 (en) | 2013-04-30 | 2015-04-10 | Oreal | AEROSOL DEVICE BASED ON SEBUM ABSORBENT POWDER AND CALCIUM CARBONATE |
FR3004901B1 (en) | 2013-04-30 | 2016-02-12 | Oreal | MULTI-ORIFICE DIFFUSION AEROSOL DEVICE FOR DRY WASHING HAIR |
US20160120771A1 (en) | 2013-05-24 | 2016-05-05 | L'oreal | Cosmetic composition comprising an aqueous phase and a fatty phase that are visually distinct |
FR3006185B1 (en) | 2013-06-03 | 2015-08-07 | Oreal | COSMETIC COMPOSITION COMPRISING NONIONIC ASSOCIATIVE POLYMERS AND SULFONATE ANIONIC SURFACTANTS, AND COSMETIC TREATMENT METHOD |
FR3006184B1 (en) | 2013-06-03 | 2015-07-31 | Oreal | COSMETIC COMPOSITION COMPRISING NON-IONIC ASSOCIATIVE POLYMERS AND NON-IONIC SURFACTANTS, AND COSMETIC TREATMENT METHOD |
FR3006187B1 (en) | 2013-06-03 | 2015-05-22 | Oreal | COSMETIC COMPOSITION COMPRISING NONIONIC ASSOCIATIVE POLYMERS AND AMPHOTERIC SURFACTANTS AND METHOD OF COSMETIC TREATMENT |
FR3006186B1 (en) | 2013-06-03 | 2015-05-22 | Oreal | COSMETIC COMPOSITION COMPRISING NON-IONIC ASSOCIATIVE POLYMERS AND CARBOXYLATE ANIONIC SURFACTANTS, AND COSMETIC PROCESSING METHOD |
CN105283223B (en) | 2013-06-17 | 2021-10-15 | 莱雅公司 | Cosmetic composition comprising mineral wax, fatty acid, mineral oil, surfactant, ester of fatty acid and/or fatty alcohol and fixing polymer |
FR3009680B1 (en) | 2013-08-13 | 2018-05-18 | L'oreal | COMPOSITION COMPRISING A SILANE, A PARTICULAR FIXING POLYMER AND A CELLULOSIC THICKENING POLYMER |
FR3010900B1 (en) | 2013-09-24 | 2017-02-17 | Oreal | COSMETIC COMPOSITION COMPRISING AN ASSOCIATION OF SURFACTANTS AGAINST CARBOXYLATE, ACYL-ISETHIONATE, AND ALKYL (POLY) GLYCOSIDE. |
FR3010899B1 (en) | 2013-09-24 | 2017-02-17 | Oreal | COSMETIC COMPOSITION COMPRISING AN ASSOCIATION OF ANIONIC SURFACTANTS OF CARBOXYLATE AND ACYL ISETHIONATE TYPES |
WO2015063122A1 (en) | 2013-10-30 | 2015-05-07 | L'oreal | Expanded dyeing composition comprising an inert gas, an oxidation dye and an oxyalkylenated nonionic surfactant |
FR3013972B1 (en) | 2013-12-02 | 2016-01-01 | Oreal | COMPOSITION COMPRISING AT LEAST ONE ANIONIC ASSOCIATIVE POLYMER, AT LEAST ONE ANIONIC FIXING POLYMER AND AT LEAST ONE STARCH |
FR3015252B1 (en) | 2013-12-19 | 2015-12-25 | Oreal | HIGH-BODY COMPOSITION COMPRISING HYDROGEN PEROXIDE, PERSON AND OXYETHYLENE SURFACTANTS |
FR3015272B1 (en) | 2013-12-19 | 2016-01-08 | Oreal | COLORING PROCESS USING RICH BODY COMPOSITIONS |
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FR3015273B1 (en) | 2013-12-19 | 2015-12-25 | Oreal | BODY-RICH COLORING COMPOSITION COMPRISING A MIXTURE OF OXYETHYLENE SURFACTANTS |
FR3015271B1 (en) | 2013-12-20 | 2016-01-01 | Oreal | COMPOSITION COMPRISING A PARTICULAR ACRYLIC COPOLYMER AND A THICKENING POLYMER |
FR3018684B1 (en) | 2014-03-19 | 2017-05-12 | Oreal | COSMETIC COMPOSITION COMPRISING BENEFICIAL AGENTS FOR KERATINIC MATERIALS, AND A MIXTURE OF OLEFIN SULFONATE DERIVATIVES, AND COSMETIC TREATMENT PROCESS |
EP3137039B1 (en) | 2014-05-02 | 2020-08-12 | Hercules LLC | Personal care composition for a keratin substrate comprising conditioning and/or styling cationic tetra polymer |
KR20170016386A (en) | 2014-06-02 | 2017-02-13 | 테티스, 아이엔씨. | Modified biopolymers and methods of producing and using the same |
JP6479861B2 (en) | 2014-06-18 | 2019-03-06 | ローディア オペレーションズ | Method of using compositions comprising quaternary ammonium compounds, cationic polysaccharides and non-ionic polysaccharides |
FR3022770B1 (en) | 2014-06-30 | 2016-07-29 | Oreal | AEROSOL DEVICE BASED ON CALCIUM SALT, FIXING POLYMER, SURFACTANT AND WATER |
US10780030B2 (en) | 2014-07-31 | 2020-09-22 | L'oreal | Carbonated cosmetic products containing polymers |
FR3024874B1 (en) * | 2014-08-14 | 2016-09-02 | Roquette Freres | DEXTRIN COPOLYMER WITH STYRENE AND ACRYLIC ESTER, PROCESS FOR PRODUCING THE SAME AND USE THEREOF FOR PAPER COATING |
FR3027798B1 (en) | 2014-10-29 | 2017-12-22 | Oreal | COMPOSITION BASED ON SEBUM-COATING AND / OR ABSORBENT POWDER AND ZINC SALT |
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FR3029406B1 (en) | 2014-12-08 | 2016-12-09 | Oreal | CAPILLARY COLORING PROCESS USING AT LEAST ONE DYE, ONE TITANIUM SALT, AND ANIONIC THICKENING POLYMER |
FR3029405B1 (en) | 2014-12-08 | 2019-08-02 | L'oreal | CAPILLARY COLORING PROCESS USING AT LEAST ONE COLOR, TITANIUM SALT, AND INSOLUBLE SILICATE |
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FR3030233B1 (en) | 2014-12-17 | 2016-12-09 | Oreal | COLORING COMPOSITION COMPRISING A PARA-PHENYLENEDIAMINE OXIDATION BASE, AND AN AMPHOTERIC OR CATIONIC POLYMER IN A BODY-RICH MEDIUM |
FR3030255B1 (en) | 2014-12-17 | 2016-12-23 | Oreal | COLORING COMPOSITION COMPRISING A PARA-PHENYLENEDIAMINE OXIDATION BASE, A POLYSACCHARIDE THICKENER IN A BODY-RICH MEDIUM |
FR3030237B1 (en) | 2014-12-17 | 2017-07-14 | Oreal | COLORING COMPOSITION COMPRISING A PARA-PHENYLENEDIAMINE OXIDATION BASE, AN AMPHOTERIZED ACTIVE TENSIO IN A RICH BODY MEDIUM |
FR3030234B1 (en) | 2014-12-17 | 2018-05-18 | Oreal | COLORING COMPOSITION COMPRISING A PARA-PHENYLENEDIAMINE OXIDATION BASE, NON-IONIC ACTIVE TENSIO IN A BODY-RICH MEDIUM |
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ES2964203T3 (en) | 2014-12-19 | 2024-04-04 | Oreal | Solid anhydrous cosmetic composition, preparation procedure, cosmetic treatment procedures, and associated kit |
US10717947B2 (en) | 2014-12-22 | 2020-07-21 | Rhodia Operations | Solid composition comprising a quaternary ammonium compound and polysaccharide, the process and use thereof |
FR3030231B1 (en) | 2014-12-23 | 2018-08-24 | L'oreal | USE OF A FATTY ACID ESTER FOR MATIFYING THE SKIN AND COMPOSITION COMPRISING SAID ESTER |
FR3031437B1 (en) | 2015-01-08 | 2017-01-13 | Oreal | AEROSOL DEVICE FOR SHAPING HAIR AND / OR MAINTAINING HAIR |
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KR102457934B1 (en) | 2015-01-16 | 2022-10-24 | 로디아 오퍼레이션스 | How to reduce graying of fabrics |
WO2016120291A1 (en) | 2015-01-28 | 2016-08-04 | Rhodia Operations | Composition containing ester quat, cationic polysaccharide and nonionic polysaccharide |
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FR3032119B1 (en) | 2015-01-29 | 2017-01-20 | Oreal | METHOD FOR TREATING HAIR WITH AT LEAST ONE SILICONE FUNCTIONALIZED BY AT LEAST ONE ALCOXYSILANE MOTIF, AND STEAM |
EP3262150A1 (en) | 2015-02-27 | 2018-01-03 | Rhodia Operations | Composition comprising a quaternary ammonium compound, a cationic polysaccharide and a nonionic polymer |
WO2016156486A1 (en) | 2015-04-02 | 2016-10-06 | L'oreal | Cosmetic composition comprising non-amino polyalkylsiloxanes, oxyethylenated polymers and fatty alcohols |
RU2746990C2 (en) | 2015-05-01 | 2021-04-23 | Л'Ореаль | Active agents application in chemical treatment |
JP2017025051A (en) | 2015-07-28 | 2017-02-02 | ロレアル | Composition, process, method, and use for keratin fibers |
ES2913120T3 (en) | 2015-08-04 | 2022-05-31 | Isp Investments Llc | Polymers derived from aminofunctional vinyl alcohol ethers and applications thereof |
US11384316B2 (en) | 2015-09-11 | 2022-07-12 | Isp Investments Llc | Stable laundry cleaning composition and method comprising a polyAPTAC-containing polymer |
WO2017091463A1 (en) | 2015-11-23 | 2017-06-01 | Tethis, Inc. | Coated particles and methods of making and using the same |
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WO2017091797A1 (en) | 2015-11-24 | 2017-06-01 | L'oreal | Compositions for treating the hair |
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US11395794B2 (en) | 2015-12-14 | 2022-07-26 | L'oreal | Process for treating keratin fibres using an aqueous composition comprising a combination of particular alkoxysilanes |
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US10524999B2 (en) | 2015-12-14 | 2020-01-07 | L'oreal | Composition comprising a combination of particular alkoxysilanes and a fatty substance |
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WO2017100992A1 (en) | 2015-12-15 | 2017-06-22 | Rhodia Operations | Compositions comprising quat and polysaccharides |
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WO2017107819A1 (en) | 2015-12-22 | 2017-06-29 | Rhodia Operations | Compositions comprising quat and polysaccharides |
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WO2017182401A1 (en) | 2016-04-20 | 2017-10-26 | L'oreal | Cosmetic composition comprising a particular combination of surfactants, a polyol, a cationic or amphoteric polymer and optionally a silicone. |
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FR3052060B1 (en) | 2016-06-06 | 2018-06-08 | L'oreal | PROCESS FOR TREATING KERATIN FIBERS WITH A PARTICULAR COMPOSITION AND A HEATING TOOL |
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WO2018000059A1 (en) | 2016-06-30 | 2018-01-04 | L'oreal | Compositions and methods for improving the appearance of the hair |
ES2902510T3 (en) | 2016-07-07 | 2022-03-28 | Oreal | Cosmetic composition comprising a particular combination of surfactants, a silicone, a cationic polymer, a fatty alcohol and a clay |
US20180116942A1 (en) | 2016-10-31 | 2018-05-03 | L'oreal | Compositions for chemically treated hair |
US11135150B2 (en) | 2016-11-21 | 2021-10-05 | L'oreal | Compositions and methods for improving the quality of chemically treated hair |
FR3059896A1 (en) | 2016-12-09 | 2018-06-15 | L'oreal | FLEXIBLE SOLID COSMETIC COMPOSITION COMPRISING SULFONATE ANIONIC SURFACTANTS, FATTY ESTERS AND FATTY ALCOHOLS, AND COSMETIC TREATMENT METHOD |
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US20190343742A1 (en) | 2016-12-21 | 2019-11-14 | L'oreal | Cleansing composition |
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US11433011B2 (en) | 2017-05-24 | 2022-09-06 | L'oreal | Methods for treating chemically relaxed hair |
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JP7127966B2 (en) | 2017-06-13 | 2022-08-30 | ロレアル | Combining polyion complex particles with non-polymeric bases having dissociation constants of two or more |
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FR3068246B1 (en) | 2017-06-30 | 2020-11-06 | Oreal | KERATINIC FIBER COLORING PROCESS WITH THREE DISTINCT COMPOSITIONS |
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FR3068250B1 (en) | 2017-06-30 | 2019-07-19 | L'oreal | COSMETIC COMPOSITION COMPRISING ORGANOSILANES, CATIONIC POLYMERS, LIQUID FATTY BODIES, PARTICULAR ANIONIC SURFACTANTS, AND NONIONIC AND AMPHOTERIAL SURFACTANTS, METHOD OF COSMETIC TREATMENT AND USE |
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FR3068887B1 (en) | 2017-07-17 | 2019-08-30 | L'oreal | COMPOSITION COMPRISING A FIXING POLYMER, A CATIONIC POLYMER, AN ORGANOSILANE, A NONIONIC POLYSACCHARIDE AND A WAX |
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FR3075611B1 (en) | 2017-12-21 | 2021-11-19 | Oreal | PROCESS FOR TREATMENT OF KERATINIC FIBERS IMPLEMENTING A DIRECT FLUORESCEINE HALOCHROME DYE, AN ALKALINE DEVELOPER THEN AN ACID ERASER |
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JP7179535B2 (en) | 2018-08-30 | 2022-11-29 | ロレアル | High internal oil phase emulsion composition-gel |
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US11090249B2 (en) | 2018-10-31 | 2021-08-17 | L'oreal | Hair treatment compositions, methods, and kits for treating hair |
FR3089813B1 (en) | 2018-12-12 | 2021-03-05 | Oreal | Perfume jelly |
JP7353754B2 (en) | 2018-12-14 | 2023-10-02 | ロレアル | Keratin fiber straightening method |
FR3089801B1 (en) | 2018-12-17 | 2021-09-24 | Oreal | Cosmetic composition comprising the combination of specific anionic surfactants and non-silicone liquid fatty substances, and cosmetic treatment process |
FR3089814B1 (en) | 2018-12-18 | 2021-04-02 | Oreal | PROCESS FOR TREATMENT OF KERATINIC FIBERS INCLUDING THE APPLICATION OF A COUPLING AGENT AND A PHOSPHOLIPID, COMPOSITION AND USE |
FR3103700B1 (en) | 2019-12-03 | 2024-01-19 | Oreal | Antimicrobial mixture containing 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one and 4-hydroxyacetophenone, and composition containing the same |
FR3090342B1 (en) | 2018-12-20 | 2021-05-21 | Oreal | Hair cosmetic composition in the form of a nanoemulsion comprising a particular nonionic surfactant and a propellant |
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FR3090367B1 (en) | 2018-12-20 | 2021-12-17 | Oreal | Aerosol device containing a cosmetic composition comprising a fixing polymer, a hydroxylated silicone and a powder |
FR3090348A1 (en) | 2018-12-21 | 2020-06-26 | L'oreal | Cosmetic composition comprising a particular combination of surfactants and cationic polymers |
FR3090333B1 (en) | 2018-12-21 | 2021-12-17 | Oreal | Aerosol device containing a cosmetic composition comprising an anionic surfactant, a fatty alcohol and a compressed gas |
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FR3090332B1 (en) | 2018-12-21 | 2021-07-30 | Oreal | Hair coloring process, using a titanium salt, a fatty ether and a natural dye |
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FR3095756B1 (en) | 2019-05-07 | 2021-04-16 | Oreal | PROCESS FOR SMOOTHING KERATINIC FIBERS FROM A COMPOSITION CONTAINING AN AMINO ACID |
BR112021021743A2 (en) | 2019-05-21 | 2021-12-28 | Rhodia Operations | Tissue conditioning composition |
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FR3098721B1 (en) | 2019-07-17 | 2021-06-11 | Oreal | Cosmetic composition comprising anionic and amphoteric surfactants, cationic polysaccharides and unsaturated fatty alcohols, and method of cosmetic treatment |
US11026874B2 (en) | 2019-07-31 | 2021-06-08 | L'oreal | Systems and methods for changing the color of hair |
JP2021031468A (en) | 2019-08-28 | 2021-03-01 | ロレアル | Composition containing polyion complex and texture agent |
WO2021063779A1 (en) | 2019-10-03 | 2021-04-08 | Rhodia Operations | Fabric conditioning composition comprising polymer dispersion |
US20220403293A1 (en) | 2019-10-03 | 2022-12-22 | Rhodia Operations | Polymer dispersion and a fabric conditioning composition comprising the same |
FR3103678B1 (en) | 2019-12-03 | 2022-07-01 | Oreal | Composition containing 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one, a preservative and/or antioxidant, a surfactant, and a polymer, the process for treating keratin materials from the composition |
FR3104030B1 (en) | 2019-12-06 | 2022-01-07 | Oreal | Hair treatment process comprising the application of a cosmetic care composition comprising a cationic polymer and an organosilane, then of a washing cosmetic composition |
JP7486943B2 (en) | 2019-12-16 | 2024-05-20 | ロレアル | Compositions containing cationic polysaccharides and anionic antioxidants |
FR3104426A1 (en) | 2019-12-16 | 2021-06-18 | L'oreal | Aqueous composition comprising a cationic cellulose polymer, an anionic surfactant comprising at least one cationic counterion, a fatty phase and a pigment |
FR3104425B1 (en) | 2019-12-16 | 2022-12-16 | Oreal | Aqueous composition comprising the combination of a cationic cellulosic polymer, an anionic polymer and at least one pigment |
FR3104432B1 (en) | 2019-12-17 | 2022-05-06 | Oreal | AQUEOUS COMPOSITION FOR THE TREATMENT OF KERATIN FIBERS COMPRISING A VEGETABLE OIL, A HYDROCARBONATED OIL, A GLYCEROLATED NONIONIC SURFACTANT, A POLYSACCHARIDE AND A SOLVENT |
JP2021095361A (en) | 2019-12-17 | 2021-06-24 | ロレアル | Composition comprising hyaluronic acid-based polyion complex particles |
FR3104967B1 (en) | 2019-12-18 | 2022-08-05 | Oreal | Hair treatment process |
FR3104978B1 (en) | 2019-12-18 | 2023-11-03 | Oreal | Process for the cosmetic treatment of keratin fibers comprising the application of a ready-to-use composition obtained by mixing two compositions |
FR3104984B1 (en) | 2019-12-18 | 2023-05-12 | Oreal | Aerosol device containing a cosmetic composition comprising an anionic carboxylic surfactant, an amphoteric surfactant, a nonionic surfactant, a cationic polymer, preferably associative and a propellant |
FR3104982B1 (en) | 2019-12-18 | 2023-08-18 | Oreal | Cosmetic composition comprising a particular carboxylic anionic surfactant, an amphoteric surfactant, a cationic polymer, and a non-associative acrylic thickening polymer |
FR3104985B1 (en) | 2019-12-20 | 2023-03-10 | Oreal | Composition comprising a cationic cellulosic polymer, an anionic sulphonic polymer and a fixing polymer |
FR3104997B1 (en) | 2019-12-20 | 2021-11-26 | Oreal | Process for Preparing a Composition for Coloring the Hair from a Composition In the Form of a Powder and an Aqueous Composition |
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WO2021130088A1 (en) | 2019-12-24 | 2021-07-01 | L'oreal | Cosmetic composition comprising a polymer comprising at least one cationic (meth)acrylamide unit, a particular silicone and at least one surfactant |
US20210196609A1 (en) | 2019-12-26 | 2021-07-01 | L'oreal | Compositions and methods for styling hair |
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US11826451B2 (en) | 2019-12-31 | 2023-11-28 | L'oreal | Compositions for treating hair |
WO2021171909A1 (en) | 2020-02-26 | 2021-09-02 | L'oreal | Composition comprising positively charged polyion complex |
FR3108511A1 (en) | 2020-03-26 | 2021-10-01 | L'oreal | Composition comprising a polyion complex and a fatty alcohol |
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FR3108841B1 (en) | 2020-04-06 | 2023-11-03 | Algotherapeutix | TOPICAL PHARMACEUTICAL COMPOSITION IN AQUEOUS GEL FORM COMPRISING AT LEAST AMITRIPTYLINE |
US11946026B2 (en) | 2020-06-04 | 2024-04-02 | International Flavors & Fragrances Inc. | Fabric care composition and method for improving fragrance intensity with isopropyl myristate |
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US20230404872A1 (en) | 2020-11-06 | 2023-12-21 | L'oreal | Composition for keratin fibers |
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EP4154974A1 (en) | 2021-09-23 | 2023-03-29 | International Flavors & Fragrances Inc. | Biodegradable microcapsules |
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FR3131528B1 (en) | 2021-12-30 | 2024-03-01 | Oreal | Cosmetic packaging article comprising a solid composition |
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EP4212239A1 (en) | 2022-01-14 | 2023-07-19 | International Flavors & Fragrances Inc. | Biodegradable prepolymer microcapsules |
FR3132637A1 (en) | 2022-02-15 | 2023-08-18 | L'oreal | Cosmetic or dermatological composition comprising a merocyanine and a polyionic complex |
WO2023206341A1 (en) | 2022-04-29 | 2023-11-02 | L'oreal | Composition for conditioning the hair |
WO2023228870A1 (en) | 2022-05-25 | 2023-11-30 | L'oreal | Composition for coloring keratin fibers |
FR3137835A1 (en) | 2022-07-15 | 2024-01-19 | L'oreal | Composition for coloring keratinous fibers |
FR3136161A1 (en) | 2022-06-01 | 2023-12-08 | L'oreal | Cosmetic composition comprising amino acids, hydroxylated (poly)carboxylic acids and silicones, and cosmetic treatment method |
FR3136167A1 (en) | 2022-06-01 | 2023-12-08 | L'oreal | Hair treatment process to limit the calcium content of hair |
FR3136169A1 (en) | 2022-06-01 | 2023-12-08 | L'oreal | Hair treatment process to limit hair loss of shine |
FR3136158A1 (en) | 2022-06-01 | 2023-12-08 | L'oreal | Cosmetic composition comprising amino acids, hydroxylated (poly)carboxylic acids and amphoteric surfactants, and cosmetic treatment method |
FR3136162A1 (en) | 2022-06-01 | 2023-12-08 | L'oreal | Hair treatment process comprising the application of a composition comprising amino acids and hydroxylated (poly)carboxylic acids, followed by washing the hair, and use as a pre-shampoo |
FR3136159A1 (en) | 2022-06-01 | 2023-12-08 | L'oreal | Cosmetic composition one or more amino acids, one or more (poly) hydroxylated C2-C8 carboxylic acids and one or more salts of (poly) hydroxylated C2-C8 carboxylic acids, and cosmetic treatment method |
FR3136166A1 (en) | 2022-06-01 | 2023-12-08 | L'oreal | Process for cosmetic treatment of hair, comprising multiple application of a composition comprising particular amino acids and hydroxy carboxylic acids |
FR3136168A1 (en) | 2022-06-01 | 2023-12-08 | L'oreal | Hair treatment process for strengthening sensitized, weakened and/or damaged hair |
FR3136171A1 (en) | 2022-06-01 | 2023-12-08 | L'oreal | Process for cosmetic treatment of hair, comprising a washing step, a step of applying a cosmetic composition comprising amino acids and hydroxylated (poly) carboxylic acids, then a conditioning step. |
FR3136163A1 (en) | 2022-06-01 | 2023-12-08 | L'oreal | Cosmetic composition comprising at least 1% amino acids and at least 3% hydroxylated (poly)carboxylic acids, and cosmetic treatment method |
FR3136164A1 (en) | 2022-06-01 | 2023-12-08 | L'oreal | Cosmetic composition comprising amino acids, hydroxylated (poly)carboxylic acids and cationic surfactants, and cosmetic treatment method |
FR3136170A1 (en) | 2022-06-01 | 2023-12-08 | L'oreal | Cosmetic composition comprising amino acids, hydroxylated (poly)carboxylic acids and associative polymers, and cosmetic treatment method |
FR3136160A1 (en) | 2022-06-01 | 2023-12-08 | L'oreal | Cosmetic composition comprising amino acids, hydroxylated (poly)carboxylic acids and polysaccharides, and cosmetic treatment method |
FR3138311A1 (en) | 2022-07-28 | 2024-02-02 | L'oreal | Composition comprising a nonionic surfactant(s) of the alkylpolyglycoside type, a polyol(s), a C8-C30 fatty acid ester(s) of sorbitan and a polymer(s) s) cationic(s) |
WO2023237762A1 (en) | 2022-06-09 | 2023-12-14 | L'oreal | Composition comprising nonionic surfactant(s) of alkylpolyglycoside type, polyol(s), c8-c30 fatty acid ester(s) of sorbitan and cationic polymer(s) |
FR3136970A1 (en) | 2022-06-22 | 2023-12-29 | L'oreal | Keratin fiber treatment process |
FR3136977A1 (en) | 2022-06-22 | 2023-12-29 | L'oreal | WASHING COMPOSITION FOR KERATIN FIBERS COMPRISING AT LEAST ONE ANIONIC SURFACTANT, AT LEAST ONE AMPHOTERIC OR ZWITTERIONIC SURFACTANT AND AT LEAST ONE GLUCAMIDE COMPOUND |
FR3136978A1 (en) | 2022-06-22 | 2023-12-29 | L'oreal | WASHING COMPOSITION FOR KERATIN FIBERS COMPRISING AT LEAST ONE GLUCAMIDE, A (POLY)GLYCEROL ESTER AND AN ALKYL(POLY)GLYCOSIDE |
FR3137280A1 (en) | 2022-06-29 | 2024-01-05 | L'oreal | Composition comprising a peroxygen salt, an associative polymer, a non-associative polysaccharide and a hydrocarbon with a melting point greater than 25°C. |
FR3137279A1 (en) | 2022-06-29 | 2024-01-05 | L'oreal | Process for lightening keratin fibers using a composition comprising a peroxygenated salt and a fatty substance in a particular content and a composition comprising hydrogen peroxide and a fatty substance in a particular content. |
FR3137276A1 (en) | 2022-06-29 | 2024-01-05 | L'oreal | Composition comprising a peroxygenated salt, a fatty substance in a particular content, an associative polymer and a non-associative polysaccharide. |
FR3137282A1 (en) | 2022-06-29 | 2024-01-05 | L'oreal | Composition comprising a peroxygen salt, a hydrocarbon with a melting point greater than 25°C and an amino acid type compound |
FR3137277A1 (en) | 2022-06-29 | 2024-01-05 | L'oreal | Composition comprising a peroxygenated salt, a hydrocarbon with a melting point greater than or equal to 85°C and at least 10% of fatty substances. |
WO2024014310A1 (en) | 2022-07-12 | 2024-01-18 | L'oreal | Composition comprising skin care active ingredient or cellulose compound |
FR3138614A1 (en) | 2022-08-05 | 2024-02-09 | L'oreal | COMPOSITION COMPRISING AN ACTIVE INGREDIENT FOR SKIN CARE |
FR3138870A1 (en) | 2022-08-18 | 2024-02-23 | L'oreal | COMPOSITION COMPRISING A CELLULOSIC COMPOUND |
FR3138309A1 (en) | 2022-07-27 | 2024-02-02 | L'oreal | Cosmetic composition comprising 2,4-diaminopyrimidine-3-N-oxide, piroctone olamine, caffeine, and at least 0.5% by weight of particular hydroxy compound |
FR3138314A1 (en) | 2022-07-27 | 2024-02-02 | L'oreal | Cosmetic composition comprising 2,4-diaminopyrimidine-3-N-oxide, piroctone olamine, caffeine, and an extract of Eperua falcata bark |
WO2024031596A1 (en) | 2022-08-12 | 2024-02-15 | L'oreal | Composition for treating keratin fibers |
FR3141342A1 (en) | 2022-10-28 | 2024-05-03 | L'oreal | COMPOSITION COMPRISING A POLYIONIC COMPLEX BASED ON HYALURONIC ACID AND A SUPERABSORBENT POLYMER |
WO2024070749A1 (en) | 2022-09-27 | 2024-04-04 | L'oreal | Composition comprising hyaluronic acid-based polyion complex and superabsorbent polymer |
FR3140269A1 (en) | 2022-09-29 | 2024-04-05 | L'oreal | Cosmetic composition comprising a particular silicone emulsion, a particular cationic polymer, a particular anionic surfactant and an amphoteric surfactant |
FR3140282A1 (en) | 2022-09-30 | 2024-04-05 | L'oreal | Cosmetic hair care composition comprising cationic polymers and specific amino silicones, and method for cosmetic treatment of hair. |
FR3140273A1 (en) | 2022-09-30 | 2024-04-05 | L'oreal | Cosmetic hair care composition comprising at least one particular amino silicone and at least one coloring agent and/or an optical brightener, and method for cosmetic treatment of hair |
FR3140276A1 (en) | 2022-09-30 | 2024-04-05 | L'oreal | Cosmetic hair care composition comprising particular anionic surfactants and particular amino silicones, and method for cosmetic treatment of hair. |
FR3140279A1 (en) | 2022-09-30 | 2024-04-05 | L'oreal | Cosmetic hair care composition comprising at least one particular amino silicone and at least one non-silicone fatty substance, and method for cosmetic treatment of hair |
FR3140280A1 (en) | 2022-09-30 | 2024-04-05 | L'oreal | Cosmetic hair care composition comprising at least one particular amino silicone and at least one polyol, and cosmetic treatment method |
FR3140281A1 (en) | 2022-09-30 | 2024-04-05 | L'oreal | Method for cosmetic treatment of hair with a cosmetic composition comprising particular amino silicones |
FR3140277A1 (en) | 2022-09-30 | 2024-04-05 | L'oreal | Cosmetic hair care composition comprising at least one particular amino silicone and at least one associative polymer, and cosmetic hair treatment method |
FR3140283A1 (en) | 2022-09-30 | 2024-04-05 | L'oreal | Cosmetic hair care composition comprising anionic and amphoteric surfactants in a particular weight ratio and particular amino silicones, and method for cosmetic treatment of hair. |
FR3140271A1 (en) | 2022-09-30 | 2024-04-05 | L'oreal | Cosmetic hair care composition comprising anionic and/or amphoteric surfactants, and specific amino silicones, and cosmetic hair treatment method. |
FR3140274A1 (en) | 2022-09-30 | 2024-04-05 | L'oreal | Cosmetic hair care composition comprising at least one particular amino silicone and at least one thickening agent |
WO2024075555A1 (en) | 2022-10-04 | 2024-04-11 | L'oreal | Composition comprising large amount of polyol |
FR3142086A1 (en) | 2022-11-17 | 2024-05-24 | L'oreal | COMPOSITION COMPRISING A LARGE QUANTITY OF POLYOL |
FR3140544A1 (en) | 2022-10-10 | 2024-04-12 | L'oreal | DETERGENT AND EXFOLIATING HAIR COSMETIC COMPOSITION COMPRISING SALICYLIC ACID AND SUSPENDED PARTICLES |
FR3141338A1 (en) | 2022-10-26 | 2024-05-03 | L'oreal | Solid composition comprising a cationic surfactant, a starch, a silicone and a non-silicone fatty substance |
FR3141336A1 (en) | 2022-10-26 | 2024-05-03 | L'oreal | SOLID COMPOSITION COMPRISING A CATIONIC SURFACTANT, A STARCH AND A SPECIFIC QUANTITY OF C1-6 CARBOXYLIC ACID |
FR3141335A1 (en) | 2022-10-26 | 2024-05-03 | L'oreal | Solid composition comprising a cationic surfactant, a starch, a polyol and a cationic polymer |
FR3141337A1 (en) | 2022-10-26 | 2024-05-03 | L'oreal | SOLID COMPOSITION COMPRISING A CATIONIC SURFACTANT, A STARCH, AN AMPHOTERIC SURFACTANT AND A FAT |
FR3141339A1 (en) | 2022-10-26 | 2024-05-03 | L'oreal | SOLID COMPOSITION COMPRISING A CATIONIC SURFACTANT, TWO STARCHES, A LIQUID FAT AND A SPECIFIC QUANTITY OF WATER |
FR3141333A1 (en) | 2022-10-26 | 2024-05-03 | L'oreal | Cosmetic packaging article comprising a solid composition comprising a phosphated starch |
WO2024097256A1 (en) | 2022-10-31 | 2024-05-10 | L'oreal | Systems and methods for stabilizing compositions, and compositions comprising the systems |
WO2024094537A1 (en) | 2022-11-03 | 2024-05-10 | L'oreal | Composition comprising a particular silicone, a particular silicone emulsion, a particular vinylic polymer and surfactants |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1123110B (en) * | 1960-09-14 | 1962-02-01 | Hoechst Ag | Process for the polymerization of water-soluble monomers |
US3656884A (en) * | 1967-08-17 | 1972-04-18 | Takuji Okaya | Process for the preparation of grafted solid materials of water-affinitive polymers |
US3809664A (en) * | 1973-08-16 | 1974-05-07 | Us Agriculture | Method of preparing starch graft polymers |
US3957739A (en) * | 1974-11-27 | 1976-05-18 | Nobel Hoechst Chimie | Process of production of water-soluble linear polymers of very high molecular weight |
US3976552A (en) * | 1975-08-13 | 1976-08-24 | The United States Of America As Represented By The Secretary Of Agriculture | Water-soluble graft polymers produced by an outwardly dry radiation polymerization process |
US4028290A (en) * | 1975-10-23 | 1977-06-07 | Hercules Incorporated | Highly absorbent modified polysaccharides |
-
1977
- 1977-12-15 US US05/860,951 patent/US4131576A/en not_active Expired - Lifetime
-
1978
- 1978-09-11 CA CA311,047A patent/CA1084643A/en not_active Expired
- 1978-09-14 DE DE2840010A patent/DE2840010C3/en not_active Expired
- 1978-09-25 GB GB7837991A patent/GB2010291B/en not_active Expired
- 1978-09-25 NL NL7809707A patent/NL167705C/en not_active IP Right Cessation
- 1978-09-29 FR FR7827883A patent/FR2411848A1/en active Granted
- 1978-10-02 BE BE78190869A patent/BE870955A/en not_active IP Right Cessation
- 1978-11-08 JP JP13687278A patent/JPS5483987A/en active Pending
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2345431A2 (en) | 2002-06-11 | 2011-07-20 | Basf Se | Method for producing esters from polyalcohols |
EP2345432A2 (en) | 2002-06-11 | 2011-07-20 | Basf Se | Method for producing esters from polyalcohols |
EP1736508A1 (en) | 2005-06-22 | 2006-12-27 | Basf Aktiengesellschaft | Hydrogel-forming polymers with increased permeability and high absorption capacity |
Also Published As
Publication number | Publication date |
---|---|
FR2411848A1 (en) | 1979-07-13 |
JPS5483987A (en) | 1979-07-04 |
US4131576A (en) | 1978-12-26 |
GB2010291A (en) | 1979-06-27 |
GB2010291B (en) | 1982-03-03 |
FR2411848B1 (en) | 1981-04-10 |
BE870955A (en) | 1979-02-01 |
DE2840010B2 (en) | 1981-07-16 |
NL7809707A (en) | 1979-06-19 |
NL167705B (en) | 1981-08-17 |
DE2840010A1 (en) | 1979-06-21 |
CA1084643A (en) | 1980-08-26 |
NL167705C (en) | 1982-01-18 |
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